A new entry to Amaryllidaceae alkaloids from carbohydrates: Total synthesis of (+)-vittatine

Masahiro Bohno; Hidetomo Imase; Noritaka Chida

doi:10.1039/b402762k

A new entry to Amaryllidaceae alkaloids from carbohydrates: Total synthesis of (+)-vittatine

Masahiro Bohno, Hidetomo Imase, Noritaka Chida

Department of Applied Chemistry

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

32 Citations (Scopus)

Abstract

The stereoselective and chiral synthesis of the Amaryllidaceae alkaloid, (+)-vittatine 1, is described; the quaternary carbon in 1 was generated by Claisen rearrangement of a cyclohexenol derived from D-glucose by way of a Ferrier's carbocyclisation reaction and a hexahydroindole skeleton was effectively constructed by intramolecular aminomercuration-demercuration, followed by Chugaev reaction.

Original language	English
Pages (from-to)	1086-1087
Number of pages	2
Journal	Chemical Communications
Volume	4
Issue number	9
DOIs	https://doi.org/10.1039/b402762k
Publication status	Published - 2004

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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A new entry to Amaryllidaceae alkaloids from carbohydrates: Total synthesis of (+)-vittatine

Abstract

ASJC Scopus subject areas

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