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Novel assembly of cyclic ethers by coupling alpha-chlorosulfides and alcohols
Masayuki Inoue1, Guang Xing Wang, Jin Wang
1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Organic Letters
|September 27, 2002
Abstract:
A novel protocol for assembling polycyclic ethers was developed and successfully applied to the synthesis of the EFGH ring system of ciguatoxin CTX3C. A key transformation involves construction of an O,S-acetal through coupling of alpha-chlorosulfide and a secondary alcohol under mild conditions. The method is highly applicable to use with sensitive substrates and will enable the synthesis of various natural and artificial polycyclic ethers. [reaction: see text]