Total Synthesis of (–)-Stemoamide by Sequential Overman/Claisen Rearrangement

Abstract

The enantioselective total synthesis of (–)-stemoamide using Overman/Claisen rearrangement of an allylic 1,2-diol is reported. The enantiopure allylic 1,2-diol was efficiently prepared from naturally occurring dimethyl tartrate. The chirality transfer reactions through two consecutive [3,3]-sigmatropic rearrangements proceeded with complete diastereoselectivity in a one-pot process.

Key words

alkaloid - allylic compound - diol - sigmatropic rearrangement - total synthesis

• References


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