Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis.

Abstract

[formula: see text] WS9885B promotes the assembly of microtubules in vitro and displays cytotoxicity as potent as paclitaxel against several cancer cell lines. In this Letter, we propose a biogenesis for this architecturally complex bacterial metabolite from a much simpler, polyunsaturated precursor. We also present significant progress toward a convergent, enantioselective synthesis of WS9885B. Our work features a chemoselective palladium-catalyzed cross-coupling of two advanced building blocks and an uncommon Claisen-like cyclization.

• Authors: C D Vanderwal, D A Vosburg, S Weiler, E J Sorensen
• Journal: Organic letters (Org Lett) Vol. 1 Issue 4 Pg. 645-8 (Aug 26 1999) ISSN: 1523-7060 [Print] United States
• PMID: 10823194 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Antibiotics, Antineoplastic
• Heterocyclic Compounds, 4 or More Rings
• WS 9885B
• Palladium

Topics

• Antibiotics, Antineoplastic (chemical synthesis)
• Catalysis
• Cyclization
• Heterocyclic Compounds, 4 or More Rings (chemical synthesis)
• Palladium
• Stereoisomerism
• Streptomyces (chemistry)