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55 results on '"iterative synthesis"'

51. Catalytic asymmetric synthesis of mycocerosic acid

Author

Bjorn ter Horst, Adriaan J. Minnaard, Ben L. Feringa, Synthetic Organic Chemistry, Faculty of Science and Engineering, and Chemical Biology 2

Subjects
ITERATIVE SYNTHESIS, IONOMYCIN, Stereochemistry, Chemistry, Organic, EFFICIENT, Anser anser, Catalysis, Materials Chemistry, BIOSYNTHESIS, CONJUGATE ADDITION, MYCOCERANIC ACID, CONFIGURATION, Wax, Graylag goose, biology, Chemistry, Fatty Acids, Metals and Alloys, Enantioselective synthesis, Total synthesis, Mycocerosic acid, General Chemistry, General Medicine, DEOXYPROPIONATE UNITS, biology.organism_classification, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, visual_art, Ceramics and Composites, visual_art.visual_art_medium, MYCOBACTERIUM-TUBERCULOSIS, CARBOALUMINATION
Abstract

The first catalytic asymmetric total synthesis of mycocerosic acid was achieved via the application of iterative enantioselective 1,4-addition reactions and allows for the efficient construction of 1,3-polymethyl arrays with full stereocontrol; further exemplified by the synthesis of tetramethyl-decanoic acid, a component of the preen-gland wax of the graylag goose, Anser anser.

Published
2007

53. New synthesis of a stereoisomeric mixture of methyl 12-trishomofarnesoate, a juvenile hormone mimic useful in sericulture by increasing silk production.

Author

Mori K

Subjects
Animals, Bombyx chemistry, Larva chemistry, Stereoisomerism, Fatty Acids, Unsaturated chemical synthesis, Juvenile Hormones chemical synthesis, Silk chemistry
Abstract

A mixture of (E,Z)-isomers of methyl 12-trishomofarnesoate (methyl 3,7,11-trimethyl-2,6,10-pentadecatrienoate), a juvenile hormone mimic, was synthesized in nine steps (32.6% overall yield) by starting from only four commercially available materials: 2-hexanone, vinylmagnesium bromide, methyl acetoacetate and trimethyl phosphonoacetate. The mimic is useful in increasing the yield of silk by elongating the larval period of the silkworm, Bombyx mori (L.).

Published
2017
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54. Bioinspired iterative synthesis of polyketides.

Author

Zheng K, Xie C, and Hong R

Abstract

Diverse array of biopolymers and second metabolites (particularly polyketide natural products) has been manufactured in nature through an enzymatic iterative assembly of simple building blocks. Inspired by this strategy, molecules with inherent modularity can be efficiently synthesized by repeated succession of similar reaction sequences. This privileged strategy has been widely adopted in synthetic supramolecular chemistry. Its value also has been reorganized in natural product synthesis. A brief overview of this approach is given with a particular emphasis on the total synthesis of polyol-embedded polyketides, a class of vastly diverse structures and biologically significant natural products. This viewpoint also illustrates the limits of known individual modules in terms of diastereoselectivity and enantioselectivity. More efficient and practical iterative strategies are anticipated to emerge in the future development.

Published
2015
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55. Modular total syntheses of thymifodioic/incanic acids

Author

Sergio J. Álvarez-Méndez, Carlos E. Tonn, J. Roberto Saad, Celina García, and Víctor S. Martín

Subjects
Chemistry(all), ITERATIVE SYNTHESIS, Olefination, General Chemical Engineering, Total synthesis, 010402 general chemistry, 01 natural sciences, NATURAL PRODUCTS, lcsh:Chemistry, purl.org/becyt/ford/1 [https], chemistry.chemical_compound, TOTAL SYNTHESIS, purl.org/becyt/ford/1.4 [https], TERPENES, Organic chemistry, Natural products, Natural product, 010405 organic chemistry, business.industry, Terpenes, General Chemistry, Modular design, Combinatorial chemistry, 0104 chemical sciences, Iterative synthesis, lcsh:QD1-999, chemistry, Yield (chemistry), Chemical Engineering(all), business, OLEFINATION
Abstract

The first total synthesis of the bioactive natural product 2,6-(E,E)-thymifodioic acid, also called incanic acid, and its stereoisomers is described. An unified, iterative and modular strategy was envisioned, achieving the synthesis of the goals products after five reaction steps in an overall yield ranging from 8% to 16%. The key step is a non-expensive easy to perform Horner–Wadsworth–Emmons condensation. Fil: Álvarez Méndez, Sergio J.. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España Fil: Saad, José Roberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina Fil: Martín, Víctor S.. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España Fil: García, Celina. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica "Antonio González"; España

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