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An asymmetric synthesis of the macrolide antibiotic (-)-A26771B (1) has been developed wherein the stereochemistries at its C-5 and C-15 centres were installed using an ( R)-BINOL-catalyzed allylation and a lipase-catalyzed acylation respectively. Acrylation at the C-15 centre under Mitsunobu conditions followed by a ring closing metathesis provided the macrocylic skeleton, which was suitably functionalized to obtain (-)-1. The biological assay of the antibiotic and two of its precursors suggested that presence of the γ-oxo moiety and the succinate function in (-)-1 were detrimental to its antibacterial activity.

A Concise Asymmetric Synthesis of the Macrolide Antibiotic (-)-A26771B and Evaluation of its Antibacterial Activity and Some of its Precursors