The first enantioselective total synthesis of new glycolipopeptides, ieodoglucomides A and B, has been accomplished along with synthetic elaboration to their C14-epimers starting from d-glucose using β-glycosylation and Grubbs olefin cross-metathesis reactions as the key steps. The present synthetic study has indicated the ambiguity in proposed absolute stereochemistry for the natural product.

An efficient approach has been described for the synthesis of 3,5‐disubstituted isoxazoles from propargylic alcohols. The strategy involves a one‐pot p‐TSA‐catalyzed N‐propargylation of protected hydroxylamines followed by a TBAF‐mediated detosylative 5‐endo‐dig cyclization. The method was successfully used for the synthesis of various 3,5‐disubstituted isoxazoles.

A novel C5-alkylation of oxindoles using alcohols as alkylating agents under acid catalysis is described for the first time. The reactions of various benzylic, allylic and propargylic alcohols are studied to obtain the corresponding 5-substituted oxindoles in good yields.

Asymmetric total synthesis of α-isomers of ieodoglucomides A and B along with their C14-epimers has been achieved starting from D-glucose. The key reactions involved are α-glycosylation and Grubbs olefin cross-metathesis. These stereochemical analogues and their β-isomers (natural products) were screened for their effects on cytotoxicity against various cancer cell lines and it was found that a few analogues are active relative to the natural ieodoglucomides.

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