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Issue 4, 2013
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Toward a more step-economical and scalable synthesis of spongistatin 1 to facilitate cancer drug development efforts

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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

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The article was received on 08 Dec 2012, accepted on 08 Feb 2013 and first published on 11 Feb 2013


Article type: Edge Article
DOI: 10.1039/C3SC22186E
Citation: Chem. Sci., 2013,4, 1497-1501
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    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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