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The synthesis of microcarpalide and lethaloxin is described. The syntheses have further served to establish the unknown absolute configuration of (+)-lethaloxin and to show its identity with (+)- pinolidoxin.

The matched and mismatched diastereoselections are observed in the aldol reactions of a range of chiral aldehydes with the dicyclohexylboron enolate of a chiral ethyl ketone related to L-erythrulose. A C1-C9 fragment of the structure of the antifungal macrolide soraphen A1alpha is prepared in a convergent and stereoselective way.

The conjugated delta-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof are synthesized in enantiopure form. The key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.

Research has been conducted on the delta-lactone (+)-boronolide. The synthesis of this compound in the enantiopure form with L-erythrulose as a chiral starting material has been carried out and the results are reported.

The diastereoselective reactions of a number of nucleophilic reagents with a range of variously protected L-erythrulose derivatives bearing protective O-silyl, O-benzyl and O-trityl groups in various relative positions are examined. Results indicate that there is sound evidence to support the formation of alpha-chelates as the key intermediates in nucleophilic additions to the alpha,beta-dioxygenated ketones. However, there is still lack of evidence in the case of beta-chelates. Thus, proposals of their intermediacy are relegated in favor of the Felkin-Anh model.

Four epimeric pairs of epoxy lactones with clearly defined oxirane stereo structure are synthesized and usedto study the oxirane ring's gamma effects. The study fails to confirm the syn axial gamma hydrogen rule, which says that a hydrogen atom must be present on the gamma carbon atom for the epoxide ring to exert its upfield or shielding effect. Comparison between their spectra and those of the parent olefins did not show any appreciable correlation between the oxirane structure and the chemical shifts undergone by the gamma carbon atoms.

A stereoselective preparation of the cytotoxic 14-membered macrolide aspergillide A is described. The macrocyclic lactone ring is created by using a ring-closing metathesis (RCM), where the new C[double bond]C bond has exhibited the undesired Z configuration and the conversion to the required E configuration is achieved by photochemical isomerization.

The Garner's (R)-aldehyde was used to perform six step stereoselective synthesis of the glycosidase inhibitor radicamine B. The intermediate obtained from the synthesis was transformed into an intermediate of the potent [alpha]-glucosidase inhibitor nectrisine.

A stereoselective synthesis of the structure published for the natural compound named feigrisolide A is presented. A revised structure is proposed for feigrisolide A and its closely related feigrisolide B in lieu of the published structure, which did not correspond well with the natural product.

The naturally occurring gamma-lactones (+)-goniofufurone and (+)-cardiobutanolide, the two pharmacologically active products is synthesized in enantiopure from using L-erythrulose as the chiral starting material. Key steps of these syntheses are a stereoselective antiboron aldol reaction and asymmetric allylboration.

An improved procedure for the synthesis of anti aldols from protected erythrulose derivatives is reported. Various chiral, polyoxygenated d(super 3) and d(super 4) synthons are easily prepared in few steps from the aforementioned anti aldols.

Matched and mismatched diastereoselections are observed in aldol reactions of the B, B-dicyclohexylboron enolate of a protected L-erythrulose derivative with a range of chiral aldehydes. Within the Felkin-Anh paradigm, the stereochemical outcome of reactions with alpha-methyl aldehydes can be explained efficiently.

Research has been conducted on cytotoxic lactone spicigerolide and nonnatural stereoisomers. The authors describe the stereoselective synthesis of these compounds, and report the use of sugar L-rhamnose as a chiral starting material.

Several 1,3-dipolar cycloadditions of a chiral nitrone prepared from L-erythrulose is investigated. The results reveal that cycloadditions to carbon-carbon multiple bonds of dipolarophiles such as ethyl acrylate, ethyl propiolate, or dimethyl acetylenedicarboxylate were poorly stereoselective, whereas reaction with acrylonitrile provided predominantly one diastereomeric adduct.