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

Noritaka Chida; Kohji Sugihara; Seiji Amano; Seiichiro Ogawa

doi:10.1039/a604365h

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

Noritaka Chida, Kohji Sugihara, Seiji Amano, Seiichiro Ogawa

Department of Applied Chemistry

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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 language	English
Pages (from-to)	275-280
Number of pages	6
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	3
DOIs	https://doi.org/10.1039/a604365h
Publication status	Published - 1997 Feb 7

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Chemistry(all)

Cite this

Chida, N., Sugihara, K., Amano, S., & Ogawa, S. (1997). Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose. Journal of the Chemical Society - Perkin Transactions 1, (3), 275-280. https://doi.org/10.1039/a604365h

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10.1039/a604365h