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Synthesis 2022; 54(19): 4347-4352
DOI: 10.1055/s-0040-1719933
DOI: 10.1055/s-0040-1719933
paper
Enantioselective Synthesis of (+)-Agelasidine A Using Thio-Claisen Rearrangement
Generous financial support provided by a Grant-in-Aid for Scientific Research (C) (16K01916) from MEXT is gratefully acknowledged.
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719933.
- Supporting Information
Publication History
Received: 21 April 2022
Accepted after revision: 09 May 2022
Article published online:
28 June 2022
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For chirality transfer in sigmatropic rearrangements of α-silyl allyl alcohols, see: