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

Research output: Contribution to journal › Article › peer-review

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

ASJC Scopus subject areas

Chemistry(all)

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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.",

author = "Noritaka Chida and Kohji Sugihara and Seiji Amano and Seiichiro Ogawa",

year = "1997",

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T1 - Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose

AU - Chida, Noritaka

AU - Sugihara, Kohji

AU - Amano, Seiji

AU - Ogawa, Seiichiro

PY - 1997/2/7

Y1 - 1997/2/7

N2 - 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.

AB - 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.

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SN - 1472-7781

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ER -

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

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