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CONTIGNASTEROL, A HIGHLY OXYGENATED STEROID WITH THE UNNATURAL 14-BETA CONFIGURATION FROM THE MARINE SPONGE PETROSIA-CONTIGNATA THIELE, 1899

TitleCONTIGNASTEROL, A HIGHLY OXYGENATED STEROID WITH THE UNNATURAL 14-BETA CONFIGURATION FROM THE MARINE SPONGE PETROSIA-CONTIGNATA THIELE, 1899
Publication TypeJournal Article
Year of Publication1992
AuthorsBurgoyne, DL, Andersen, RJ, Allen, TM
JournalJournal of Organic Chemistry
Volume57
Pagination525-528
Date PublishedJan
Type of ArticleArticle
ISBN Number0022-3263
KeywordsC-13 ASSIGNMENTS, H-1, NMR-SPECTROSCOPY
Abstract

Contignasterol (1), a highly oxygenated steroid with the ’’unnatural’’ 14-beta proton configuration and a cyclic hemiacetal functionality in its side chain, has been isolated from the marine sponge Petrosia contignata. The structure of contignasterol was elucidated via spectroscopic studies of its tetraacetate 2 and its reduction product pentaacetate 5. Contignasterol (1) is the first example of a naturally occurring steroid with the ’’unnatural’’ 14-beta proton configuration.

URL<Go to ISI>://A1992HA46600024