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

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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
DOIs
Publication statusPublished - 1994 Nov 1

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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