Postulated biogenesis of WS9885B and progress toward an enantioselective synthesis

CD Vanderwal, DA Vosburg, S Weiler…

Index: Vanderwal, Christopher D.; Vosburg, David A.; Weiler, Sven; Sorensen, Erik J. Organic Letters, 1999 , vol. 1, # 4 p. 645 - 648

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Citation Number: 52

Abstract

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 ...