Issue 4, 2013

Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts

Abstract

An efficient, step-economical, and scalable synthesis of a diene-bearing AB spiroketal fragment of spongistatin 1, and a demonstration of its efficient coupling to an aldehyde derived from silylformylation of a homopropargyl alcohol to produce the entire complex C(13)–C(17) linker region are described. The scalability of the synthesis of the AB spiroketal fragment was demonstrated by the preparation of 34.5 grams by one chemist in ∼60 workdays, and more than 40 grams overall. With this material in hand and having established a method for its efficient coupling to the CD fragment, we have set the stage for the rapid synthesis and evaluation of a series of analogs of the CD spiroketal.

Graphical abstract: Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Dec 2012
Accepted
08 Feb 2013
First published
11 Feb 2013

Chem. Sci., 2013,4, 1497-1501

Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts

S. K. Reznik and J. L. Leighton, Chem. Sci., 2013, 4, 1497 DOI: 10.1039/C3SC22186E

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