Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose

Noritaka Chida, Kohji Sugihara, Seiji Amano, Seiichiro Ogawa

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

A chiral synthesis of the Sceletium alkaloid (-)-mesembranol 1 is described. The cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation, and the critical stereochemistry of the quaternary carbon in 1 is constructed stereoselectively via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative 14a. The perhydroindole skeleton in 1 is effectively generated by intramolecular aminomercuriation of the amino-olefin 18.

Original languageEnglish
Pages (from-to)275-280
Number of pages6
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number3
DOIs
Publication statusPublished - 1997 Feb 7

ASJC Scopus subject areas

  • Chemistry(all)

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