Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam: Total synthesis of bengamide B

Noritaka Chida, Takahiko Tobe, Katsuyuki Murai, Kaori Yamazaki, Seiichiro Ogawa

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from l-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.

Original languageEnglish
Pages (from-to)2383-2388
Number of pages6
JournalHeterocycles
Volume38
Issue number11
Publication statusPublished - 1994 Nov 1

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Caprolactam
Palladium
Biological Products
Derivatives
bengamide B
quebrachitol
cyclohexene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam : Total synthesis of bengamide B. / Chida, Noritaka; Tobe, Takahiko; Murai, Katsuyuki; Yamazaki, Kaori; Ogawa, Seiichiro.

In: Heterocycles, Vol. 38, No. 11, 01.11.1994, p. 2383-2388.

Research output: Contribution to journalArticle

Chida, Noritaka ; Tobe, Takahiko ; Murai, Katsuyuki ; Yamazaki, Kaori ; Ogawa, Seiichiro. / Stereoselective conversion of l-quebrachitol into a novel hydroxylated caprolactam : Total synthesis of bengamide B. In: Heterocycles. 1994 ; Vol. 38, No. 11. pp. 2383-2388.
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