Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum

Authors
Garcia, J Lopez, M Romeu, J
Citation
J. Garcia et al., Enantioselective synthesis of (3R,4E)-19-methylicos-4-en-1-yn-3-ol, a bioactive metabolite of the marine sponge Cribrochalina vasculum, TETRAHEDR-A, 10(13), 1999, pp. 2617-2626
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
13
Year of publication
1999
Pages
2617 - 2626
Database
ISI
SICI code
0957-4166(19990702)10:13<2617:ESO(AB>2.0.ZU;2-I
Abstract
The first stereoselective synthesis of (3R,4E)-19-methyiicos-4-en-1-yn-3-ol , an immunosuppressive and antitumoral metabolite isolated from the Caribbe an sponge Cribrochalina vasculum, has been achieved and its stereostructure has been confirmed. The key step of the synthesis involves a borane-mediat ed reduction of the parent (E)-19-methyl-1-trimethylsilylicos-4-en-1-yn-3-o ne in the presence of a chiral oxazaborolidine. (C) 1999 Elsevier Science L td. All rights reserved.