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Synfacts 2007(7): 0680-0680  
DOI: 10.1055/s-2007-968598
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

A Formal Synthesis of Psymberin

Contributor(s): Philip Kocienski
N. Shangguan, S. Kiren, L. J. Williams*
Rutgers, The State University of New Jersy, Piscataway, USA
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Publication History

Publication Date:
22 June 2007 (online)

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Significance

Psymberin is the most selective antitumor agent of the 33 members of the pederin family of sponge metabolites. The salient step of the synthesis depicted is a chemo- and stereo­selective epoxidation of the scalemic allene D with dimethyldioxirane (DMDO) to give the stable spirodiepoxide E which then rearranged to F on exposure to MeOH.