Enantioselective Synthesis of (+)-Agelasidine A Using Thio-Claisen Rearrangement

Dedicated to the memory of Hideshi Nakamura (1952–2000)

Abstract

Enantioselective synthesis of the marine natural product (+)-agelasidine A has been achieved by taking advantage of [1,3]-chirality transfer from enantiomerically enriched α-silyl farnesol through a key thio-Claisen rearrangement. The optical rotation of the hydrochloride salt of the synthetic substance confirmed that natural (+)-agelasidine A has the S-configuration at its C-10 stereogenic center.

Key words

agelasidine A - marine natural product - chirality transfer - thio-Claisen rearrangement

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