Chiral synthesis of (-)-mesembranol starting from D-glucose

Noritaka Chida, Kohji Sugihara, Seiichiro Ogawa

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The 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 reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

Original languageEnglish
Pages (from-to)901-902
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number7
DOIs
Publication statusPublished - 1994

Fingerprint

Alkaloids
Cyclohexane
Skeleton
Glucose
3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-1H-indol-6-ol

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Chiral synthesis of (-)-mesembranol starting from D-glucose. / Chida, Noritaka; Sugihara, Kohji; Ogawa, Seiichiro.

In: Journal of the Chemical Society, Chemical Communications, No. 7, 1994, p. 901-902.

Research output: Contribution to journalArticle

@article{261bd40931b140ffae0f1135f6367a9b,
title = "Chiral synthesis of (-)-mesembranol starting from D-glucose",
abstract = "The 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 reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.",
author = "Noritaka Chida and Kohji Sugihara and Seiichiro Ogawa",
year = "1994",
doi = "10.1039/C39940000901",
language = "English",
pages = "901--902",
journal = "Chemical Communications",
issn = "1359-7345",
publisher = "Royal Society of Chemistry",
number = "7",

}

TY - JOUR

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

AU - Chida, Noritaka

AU - Sugihara, Kohji

AU - Ogawa, Seiichiro

PY - 1994

Y1 - 1994

N2 - The 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 reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

AB - The 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 reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.

UR - http://www.scopus.com/inward/record.url?scp=0028350797&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0028350797&partnerID=8YFLogxK

U2 - 10.1039/C39940000901

DO - 10.1039/C39940000901

M3 - Article

AN - SCOPUS:0028350797

SP - 901

EP - 902

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 7

ER -