A Concise Stereoselective Total Synthesis of Synargentolide A from 3,4,6-Tri-O-acetyl-d-glucal

Abstract

A short and highly stereoselective synthesis of the naturally occurring, α,β-unsaturated lactone synargentolide A is described from the chiral starting material 3,4,6-tri-O-acetyl-d-glucal. Key steps of the synthesis are lactol opening, Brown’s asymmetric allylation, and a ring-closing metathesis (RCM) reaction.

Key words

3,4,6-tri-O-acetyl-d-glucal - δ-lactones - synargento­lide - Brown’s allylation - RCM

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1

Visiting Professor, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia.