STEREOSELECTIVE CONVERSION OF L-QUEBRACHITOL INTO A NOVEL HYDROXYLATED CAPROLACTAM - TOTAL SYNTHESIS OF BENGAMIDE-B

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 p...

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Bibliographic Details
Published inHeterocycles Vol. 38; no. 11; pp. 2383 - 2388
Main Authors CHIDA, N, TOBE, T, MURAI, K, YAMAZAKI, K, OGAWA, S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.11.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PALLADIUM-CATALYZED AZIDATION
ABSOLUTE-CONFIGURATION
ALLYL ESTERS
AZIDE
AMINO-ACIDS
STEREOCHEMISTRY
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Summary: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.
ISSN:0385-5414
DOI:10.3987/COM-94-6869