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Abstract: A synthesis of the β-lactone esterase inhibitors (−)-ebelactones A and B is described. The synthesis features the use of a Hoppe homoaldol reaction and a Cu(I)-mediated 1,2-metallate rearrangement of a metallated enol carbamate as key fragment linkage reactions. [ABSTRACT FROM AUTHOR]

The European green woodpecker, Picus viridis, is a widely distributed species found in the Western Palearctic region. Here, we assembled a highly contiguous genome assembly for this species using a combination of short- and long-read sequencing and scaffolded with chromatin conformation capture (Hi-C). The final genome assembly was 1.28 Gb and features a scaffold N50 of 37 Mb and a scaffold L50 of 39.165 Mb. The assembly incorporates 89.4% of the genes identified in birds in OrthoDB. Gene and repetitive content annotation on the assembly detected 15,805 genes and a ∼30.1% occurrence of repetitive elements, respectively. Analysis of synteny demonstrates the fragmented nature of the P. viridis genome when compared to the chicken (Gallus gallus). The assembly and annotations produced in this study will certainly help for further research into the genomics of P. viridis and the comparative evolution of woodpeckers. Five historical and seven contemporary samples have been resequenced and may give insights on the population history of this species., Competing Interests: Conflicts of interest The author(s) declare no conflicts of interest., (© The Author(s) 2024. Published by Oxford University Press on behalf of The Genetics Society of America.)

The spotted flycatcher (Muscicapa striata) forms with the Mediterranean flycatcher (Muscicapa tyrrhenica) a newly recognized species pair of trans-Saharan migratory passerines. These flycatchers present a nested peripatric distribution, a pattern especially unusual among high dispersal species that questions the eco-evolutionary factors involved during the speciation process. Here, we present a genome assembly for M. striata assembled using a combination of Nanopore and Illumina sequences. The final assembly is 1.08 Gb long and consists of 4,779 contigs with an N50 of 3.2 Mb. The completeness of our M. striata genome assembly is supported by the number of BUSCO (95%) and ultraconserved element (UCE) (4889/5041; 97.0%) loci retrieved. This assembly showed high synteny with the Ficedula albicollis reference genome, the closest species for which a chromosome-scale reference genome is available. Several inversions were identified and will need to be investigated at the family level., (© The Author(s) 2023. Published by Oxford University Press on behalf of Society for Molecular Biology and Evolution.)

Due to the omnipresence of chiral organofluorine compounds in pharmaceutical, agrochemical, and material chemistry, the development of enantioselective methods for their preparation is highly desirable. In the present study, the enantioselective organocatalyzed acylation of α,α-difluorohydrins using a commercially available chiral isothiourea is reported through a kinetic resolution (KR) process. It reveals that the difluoromethylene moiety (C(sp 3 )F 2 ) can serve as a directing group through electrostatic fluorine-cation interactions, greatly improving the enantioselectivity of the KR. In this context, a broad range of fluorinated alcohols such as valuable 4,4-difluoro-1,3-diols could be synthesized with exquisite enantiocontrol (typically >99:1 er). Turning to 2,2-difluoro-1,3-diols, we also demonstrated that aromatic and fluorinated groups were mutually compatible to provide the expected enantioenriched adducts with >99:1 er., (© 2021 Wiley-VCH GmbH.)

The stereocontrol of tertiary alcohols represents a recurrent challenge in organic synthesis. In the present paper, we describe a simple, efficient, and indirect method to enantioselectively prepare tertiary alcohols through a chiral isothiourea catalyzed selective acylation of adjacent secondary alcohols. This transformation enables the kinetic resolution (KR) of easily prepared racemic diastereoenriched secondary/tertiary diols providing both monoesters and starting diols in highly enantioenriched forms ( s -value >200).

Each year, billions of songbirds cross large ecological barriers during their migration. Understanding how they perform this incredible task is crucial to predict how global change may threaten the safety of such journeys. Earlier studies based on radar suggested that most songbirds cross deserts in intermittent flights at high altitude, stopping in the desert during the day, while recent tracking with light loggers suggested diurnal prolongation of nocturnal flights and common non-stop flights for some species. We analyzed light intensity and temperature data obtained from geolocation loggers deployed on 130 individuals of ten migratory songbird species, and show that a large variety of strategies for crossing deserts exists between, but also sometimes within species. Diurnal stopover in the desert is a common strategy in autumn, while most species prolonged some nocturnal flights into the day. Non-stop flights over the desert occurred more frequently in spring than in autumn, and more frequently in foliage gleaners. Temperature recordings suggest that songbirds crossed deserts with flight bouts performed at various altitudes according to species and season, along a gradient ranging from low above ground in autumn to probably >2000 m above ground level, and possibly at higher altitude in spring. High-altitude flights are therefore not the general rule for crossing deserts in migrant songbirds. We conclude that a diversity of migration strategies exists for desert crossing among songbirds, with variations between but also within species.

Habitat destruction is the single greatest anthropogenic threat to biodiversity. Decades of research on this issue have led to the accumulation of hundreds of data sets comparing species assemblages in larger, intact, habitats to smaller, more fragmented, habitats. Despite this, little synthesis or consensus has been achieved, primarily because of non-standardized sampling methodology and analyses of notoriously scale-dependent response variables (i.e., species richness). To be able to compare and contrast the results of habitat fragmentation on species' assemblages, it is necessary to have the underlying data on species abundances and sampling intensity, so that standardization can be achieved. To accomplish this, we systematically searched the literature for studies where abundances of species in assemblages (of any taxa) were sampled from many habitat patches that varied in size. From these, we extracted data from several studies, and contacted authors of studies where appropriate data were collected but not published, giving us 117 studies that compared species assemblages among habitat fragments that varied in area. Less than one-half (41) of studies came from tropical forests of Central and South America, but there were many studies from temperate forests and grasslands from all continents except Antarctica. Fifty-four of the studies were on invertebrates (mostly insects), but there were several studies on plants (15), birds (16), mammals (19), and reptiles and amphibians (13). We also collected qualitative information on the length of time since fragmentation. With data on total and relative abundances (and identities) of species, sampling effort, and affiliated meta-data about the study sites, these data can be used to more definitively test hypotheses about the role of habitat fragmentation in altering patterns of biodiversity. There are no copyright restrictions. Please cite this data paper and the associated Dryad data set if the data are used in publications., (© 2019 The Authors. Ecology © 2019 The Ecological Society of America.)

Molecular phylogenetic studies of woodpeckers (Picidae) have generally focused on relationships within specific clades or have sampled sparsely across the family. We compared DNA sequences of six loci from 203 of the 217 recognized species of woodpeckers to construct a comprehensive tree of intrafamilial relationships. We recovered many known, but also numerous unknown, relationships among clades and species. We found, for example, that the three picine tribes are related as follows (Picini, (Campephilini, Melanerpini)) and that the genus Dinopium is paraphyletic. We used the tree to analyze rates of diversification and biogeographic patterns within the family. Diversification rate increased on two occasions during woodpecker history. We also tested diversification rates between temperate and tropical species but found no significant difference. Biogeographic analysis supported an Old World origin of the family and identified at least six independent cases of New World-Old World sister relationships. In light of the tree, we discuss how convergence, mimicry, and potential cases of hybridization have complicated woodpecker taxonomy., (Copyright © 2017 Elsevier Inc. All rights reserved.)

The dynamics of species accumulation of African terrestrial vertebrates over time remains underexplored in comparison with those in the New World, despite Africa hosting about 25% of the world's avian diversity. This lack of knowledge hampers our understanding of the fundamental processes that drive biodiversity and the dynamics of speciation. To begin to address this gap, we reconstructed species-level phylogenies of two unrelated clades of African woodpeckers (12 species of Geocolaptes/Campethera and 13 species of Chloropicus/Mesopicos/Dendropicos/Ipophilus) that diverged from their closest Indo-Malayan relatives at similar times. Our results demonstrate that the current taxonomy is misleading: three (Campethera, Dendropicos and Mesopicos) out of four polytpic genera/subgenera are not monophyletic. Our results also show that current estimates of diversity at the species level are significantly understated, as up to 18 species for the 'Campethera clade' and 19 for the 'Dendropicos clade' could be recognized. The first splits within both clades involve species that are largely restricted to the Guineo-Congolian biogeographic regions, followed by later adaptations to particular habitats (forest versus savannah) and colonization of other regions (e.g. Southern Africa), each of which occurred multiple times in both clades. Assuming a conservative species delimitation scheme, our results indicate that diversification rates are decreasing through time for both clades. Applying a more extreme species recognition scheme (18 and 19 species for the Campethera and Dendropicos clades, respectively), our results support a decrease in diversification rates only for the Dendropicos clade and thus underline the importance of the number of species included in our diversification analyses. Greater ecological diversity of the Campethera clade where multiple species exhibit either an arboreal or terrestrial foraging strategy might explain the constant diversification rates through time we found under the eighteen species scheme., (Copyright © 2017 Elsevier Inc. All rights reserved.)

Species complexes that have undergone recent radiations are often characterized by extensive allele sharing due to recent ancestry and (or) introgressive hybridization. This can result in discordant evolutionary histories of genes and heterogeneous genomes, making delineating species limits difficult. Here we examine the phylogenetic relationships among a complex group of birds, the white-headed gulls (Aves: Laridae), which offer a unique window into the speciation process due to their recent evolutionary history and propensity to hybridize. Relationships were examined among 17 species (61 populations) using a multilocus approach, including mitochondrial and nuclear intron DNA sequences and microsatellite genotype information. Analyses of microsatellite and intron data resulted in some species-based groupings, although most species were not represented by a single cluster. Considerable allele and haplotype sharing among white-headed gull species was observed; no locus contained a species-specific clade. Despite this, our multilocus approach provided better resolution among some species than previous studies. Interestingly, most clades appear to correspond to geographic locality: our BEAST analysis recovered strong support for a northern European/Icelandic clade, a southern European/Russian clade, and a western North American/canus clade, with weak evidence for a high latitude clade spanning North America and northwestern Europe. This geographical structuring is concordant with behavioral observations of pervasive hybridization in areas of secondary contact. The extent of allele and haplotype sharing indicates that ecological and sexual selection are likely not strong enough to complete reproductive isolation within several species in the white-headed gull complex. This suggests that just a few genes are driving the speciation process., (Published by Elsevier Inc.)

The pied woodpecker assemblage historically included the widespread genera Picoides and Dendrocopos. The assignment of species to either of these two genera has for long puzzled systematists due to their overall plumage similarity. Recent molecular studies not only suggested that both of these genera are not monophyletic, but also that four other genera, the African Dendropicos the South American Veniliornis and two Asian monospecific genera (Hypopicus and Sapheopipo) are nested within the Dendrocopos-Picoides clade. Yet, our current understanding of the phylogeny and taxonomy of this group is still very partial because several distinctive Old World species that have been assigned to different genera throughout their taxonomic history have not been sampled yet. Here, using DNA sequence data gathered from four loci, we reconstructed a species level phylogeny of the Indo-Malayan and Palearctic Pied Woodpeckers to understand the phylogenetic relationships and biogeographic history of the Eurasian species with respect to African and New World lineages. Our phylogenetic analyses revealed nine strongly supported clades within the Dendropicini. Noticeably, two species that had disputed affinities at the genus level clustered in clades with species from the same biogeographical region: the Brown-backed Woodpecker (D. obsoletus) is nested in Dendropicos and the Arabian Woodpecker (D. dorae) is related to two Eurasian species, the Brown-fronted (D. auriceps) and Middle-spotted woodpeckers (D. medius). The nine clades have a strong biogeographic component and very few dispersal event among bioregions occurred. For example, the African species formed a clade, suggesting that only one dispersal event is needed to explain the presence of Dendropicini in Africa. Based on our phylogenetic results, we propose a new classification of the Dendropicini that recognizes nine genera., (Copyright © 2015 Elsevier Inc. All rights reserved.)

The ever increasing number of analysed loci in phylogenetics has not only allowed resolution of some parts of the Tree of Life but has also highlighted parts of the tree where incongruent signals among loci were detected. Previous molecular studies suggested conflicting relationships for the New World genus Campephilus, being either associated to the Megapicini or Dendropocini. Yet, the limited number of analysed loci and the use of the concatenation approach to reconstruct the phylogeny prevented the disentanglement of lineage sorting and introgression as causal explanation of this topological conflict. We sequenced four mitochondrial, nine autosomal and three Z-linked loci and used a method that incorporates population level processes into the phylogenetic framework to understand which process (lineage sorting of genetic polymorphism or hybridization/introgression) best explains this conflict. Our analyses revealed that the autosomal FGB intron-7 and to a lesser extent the Z-linked loci have a different phylogenetic history from the mitochondrial loci and some other nuclear loci we analysed. We suggest that this conflicting pattern is the result of introgression consecutive to a hybridization event at the time when members of the Campephilus and melanerpine (Melanerpes and Sphyrapicus) lineages colonized the New World. The case of Campephilus highlights that the mitochondrial genome does not always carry the 'wrong' phylogenetic signal after a past hybridization event. Indeed, we here emphasise that the signature of such event can also be detected in the nuclear genome. With the ongoing increase in the number of loci analysed in phylogenetic studies, it is very likely that further cases will be discovered. Our current results indicate that (1) the genus Campephilus is related to the Asian genera Blythipicus, Chrysocolaptes and Reinwardtipicus, in accordance with morphological data and (2) that the nuclear genome of Campephilus is likely the mixture of two unrelated lineages. Yet, further work with a denser sampling of loci is necessary to evaluate the extant of the Sphyrapicus/Melanerpes lineage nuclear genome that introgressed into the Campephilus genome., (Copyright © 2013 Elsevier Inc. All rights reserved.)

The synthesis of various heterocycles and carbocycles (tetrahydrofurans, pyrrolidines, cyclopentanes) has been achieved by using new and efficient ionic addition/cyclization sequences. Nitroolefins play an important role in the Michael addition induced ring-closing reactions (MIRC) reported in the present article, with various substituted alcohols, amines, Grignard reactants, or malonate derivatives acting as the nucleophile partner. The optimized cascade reactions were high yielding in most cases and highly stereoselective, creating up to three stereogenic centers starting from achiral substrates.

Background: The island of Madagascar and surrounding volcanic and coralline islands are considered to form a biodiversity hotspot with large numbers of unique taxa. The origin of this endemic fauna can be explained by two different factors: vicariance or over-water-dispersal. Deciphering which factor explains the current distributional pattern of a given taxonomic group requires robust phylogenies as well as estimates of divergence times. The lineage of Indian Ocean scops-owls (Otus: Strigidae) includes six or seven species that are endemic to Madagascar and portions of the Comoros and Seychelles archipelagos; little is known about the species limits, biogeographic affinities and relationships to each other. In the present study, using DNA sequence data gathered from six loci, we examine the biogeographic history of the Indian Ocean scops-owls. We also compare the pattern and timing of colonization of the Indian Ocean islands by scops-owls with divergence times already proposed for other bird taxa., Results: Our analyses revealed that Indian Ocean islands scops-owls do not form a monophyletic assemblage: the Seychelles Otus insularis is genetically closer to the South-East Asian endemic O. sunia than to species from the Comoros and Madagascar. The Pemba Scops-owls O. pembaensis, often considered closely related to, if not conspecific with O. rutilus of Madagascar, is instead closely related to the African mainland O. senegalensis. Relationships among the Indian Ocean taxa from the Comoros and Madagascar are unresolved, despite the analysis of over 4000 bp, suggesting a diversification burst after the initial colonization event. We also highlight one case of putative back-colonization to the Asian mainland from an island ancestor (O. sunia). Our divergence date estimates, using a Bayesian relaxed clock method, suggest that all these events occurred during the last 3.6 myr; albeit colonization of the Indian Ocean islands were not synchronous, O. pembaensis diverged from O. senegalensis about 1.7 mya while species from Madagascar and the Comoro diverged from their continental sister-group about 3.6 mya. We highlight that our estimates coincide with estimates of diversification from other bird lineages., Conclusion: Our analyses revealed the occurrence of multiple synchronous colonization events of the Indian Ocean islands by scops-owls, at a time when faunistic exchanges involving Madagascar was common as a result of lowered sea-level that would have allowed the formation of stepping-stone islands. Patterns of diversification that emerged from the scops-owls data are: 1) a star-like pattern concerning the order of colonization of the Indian Ocean islands and 2) the high genetic distinctiveness among all Indian Ocean taxa, reinforcing their recognition as distinct species.

Previous studies have suggested that the woodpecker genus Picus (Aves: Picidae) may not be monophyletic. In order to evaluate this hypothesis, we analyzed DNA sequences from all but two species of Picus, as well as from representatives of all genera in the tribe Malarpicini, within which Picus is nested. We sequenced seven loci (four autosomal, one Z-linked and two mitochondrial) with different evolutionary dynamics. The species currently placed in Picus fall into two subclades that may not form a monophyletic assemblage. Consequently, we propose to place miniaceus Pennant 1769, flavinucha Gould 1834 and mentalis Temminck 1825 in the genus Chrysophlegma Gould, 1850, while the remaining species are retained in Picus. The inclusion in our study of representatives of all genera included in the tribe Malarpicini, a group of woodpeckers which has proven difficult to resolve in several previous molecular studies, also allowed us to determine the earliest divergences within this clade. The results suggest that the low level of basal resolution in Malarpicini is attributable to multiple cladogenetic events in a short period of time rather than insufficient character sampling. This conclusion is supported by the observation of nucleotide insertion-deletions that support mutually exclusive phylogenetic hypotheses in different gene trees. We attribute this pattern of incongruent indels, together with short internodes in the tree, to incomplete lineage sorting.

We address the phylogenetic relationships of the drongos (Dicruridae) at the species-level using sequences from two nuclear (myoglobin intron-2 and c-mos) and two mitochondrial (ND2 and cytochrome b) loci. The resulting phylogenetic tree shows that the most basal species is D. aeneus, followed in the tree by a trichotomy including (1) the Asian D. remifer, (2) a clade of all African and Indian Ocean islands species as well as two Asian species (D. macrocercus and D. leucophaeus) and (3) a clade that includes all other Asian species as well as two Australasian species (D. megarhynchus and D. bracteatus). Our phylogenetic hypotheses are compared to [Mayr, E., Vaurie, C., 1948. Evolution of the family Dicruridae (Birds). Evolution 2, 238-265.] hypothetical family "tree" based on traditional phenotypic analysis and biogeography. We point out a general discrepancy between the so-called "primitive" or "unspecialized" species and their position in the phylogenetic tree, although our results for other species are congruent with previous hypotheses. We conduct dating analyses using a relaxed-clock method, and propose a chronology of clades formation. A particular attention is given to the drongo radiation in Indian Ocean islands and to the extinction-invasion processes involved. The first large diversification of the family took place both in Asia and Africa at 11.9 and 13.3Myr, respectively, followed by a dispersal event from Africa to Asia at ca 10.6Myr; dispersal over Wallace line occurred later at ca 6Myr. At 5Myr, Principe and Indian Ocean Islands have been colonized from an African ancestor; the most recent colonization event concerned Anjouan by an immigrating population from Madagascar.

1. Landscape connectivity may greatly influence the distribution of animals when it alters their movements and their ability to reach food patches. Depending on their foraging behaviour, organisms may or may not adapt to anthropogenic changes in landscape connectivity and may eventually undergo local extinctions. 2. Recent studies underlined the need to use indicators of functional landscape connectivity based on the behaviour and movement abilities of studied animals to better link landscape structure to ecological processes in disturbed and fragmented areas. 3. The objectives of this study were: to elaborate an index of functional connectivity for Rhinophylla pumilio, a Neotropical understorey frugivorous bat; to use this index to investigate the possible mechanisms controlling its distribution and sustainability in a fragmented landscape; and to test whether this index could be applied to other species of the same guild. 4. We pursued a 10-year bat mist-net survey, coupled to local estimates of food availability, in a mature forest of French Guiana that was recently fragmented by the completion of a reservoir lake. The 18 sampling sites range from undisturbed continuous forest sites to small remote forest fragments. A connectivity value, based on radio-tracking surveys, was attributed to each site. Connectivity measures mean forest cover within neighbouring landscape units, weighted by the probability that bats would use them, as estimated by frequency distribution of flight distance data. 5. The abundance of R. pumilio was positively correlated with landscape connectivity and not correlated with local food availability. Its foraging strategy has evolved in response to the highly scattered distribution of its fruit resource. In spite of its high mobility, R. pumilio apparently failed to exploit a food resource that is distributed patchily over a low-connective habitat because its foraging movements are not well adapted to habitat disruptions. 6. The connectivity index contributed to explain general tendencies of abundance variations in other understorey frugivorous bats, although the spatial scale we examined was probably too small for these species. We make recommendations to adapt a functional connectivity index to species whose large-scale movements are difficult to survey.

The Al(OTf)(3)-catalyzed cycloisomerization of unactivated unsaturated alcohols was studied from experimental and theoretical points of view. A series of cyclic ethers was obtained in excellent yields and regioselectivities. This catalyst system provides one of the most straightforward routes to cyclic ethers with Markovnikov-type regioselectivity under mild conditions. Theoretical and NMR studies were carried out in order to better determine the mechanism of this reaction. The NMR studies were in agreement with preferential complexation of Al(OTf)(3) to the oxygen atom of the unsaturated alcohol, but did not exclude complexation to the double bond of the alcohol. Theoretical calculations indicated strong acidification of the hydroxyl proton when Al(OTf)(3) was complexed to the alcohol oxygen atom. A plausible catalytic cycle for the Al(OTf)(3)-catalyzed intramolecular hydroalkoxylation of unactivated olefins is proposed.

The Crested Lark has a very complex taxonomy, partly as a result of a strong variation in plumage ground color seemingly linked with environmental factors. However, large variations in body size and bill shape further complicate the situation in the Maghreb. In this paper, we first present a set of hypotheses to explain patterns of morphological variation around the Mediterranean Sea. A phylogeographical analysis covering all major biogeographical areas in the species' range is then performed to test these scenarios. Three mtDNA groups with distinct geographical distribution were identified. The randonii clade (= G. (c.) randonii) is endemic from central Maghreb and is phylogenetically basal relative to cristata and senegallensis. These two latter groups are much more widespread. The cristata clade is found in NW Morocco, throughout Europe and W Asia and in NE Africa, while senegallensis regroups the populations sampled in the Western Sub-Saharan Africa and in NE Maghreb (E Algeria, Tunisia). A combination of genetic and paleoenvironmental evidences supports a scenario of allopatric differentiation of these two lineages outside the Maghreb, with subsequent range expansion leading to their secondary presence in the Maghreb. However, the alternative hypothesis of differentiation in two, or even three separate Maghreb refuges cannot be completely dismissed with the present data. Interestingly, the Sahara desert and the Gibraltar Strait did not act as permanent barriers to dispersal in this species. In addition, the populations in the Maghreb are consistently longer-billed than their closest relatives, suggesting a role for natural selection or phenotypic plasticity.

We measured genetic differentiation among species of large white-headed gulls using mitochondrial (cytochrome b haplotypes) and nuclear (microsatellites) markers. Additional information was added using a previously published study of allozymes on the same species. Levels of differentiation among species at nuclear markers are much lower than would be expected for avian species and are not concordant with the level of differentiation in mitochondrial markers. This discrepancy is best explained by a combination of recent species origin and interspecific gene flow after speciation. The data also suggest that female-mediated gene flow is reduced compared to male-mediated gene flow, either due to behavioral bias or due to stronger counterselection of female hybrids in accordance with Haldane's rule for ZW species. Whatever the reasons for the low differentiation of the species' nuclear gene pools, the extensive similarity of their nuclear genome demonstrates that selection on a limited number of characters is an important factor in establishing and maintaining clear-cut phenotypic differences between these species and suggests that the number of loci involved in this process is quite low. This situation may not be exceptional in birds, indeed a number of studies have found similarly low level of differentiation in nuclear markers among congeneric bird species, although usually based on a single set of markers. Because hybridization is a widespread phenomenon in birds, many of these cases might be due to interspecific gene flow.