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Issue 30, 2017
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First stereoselective total synthesis of brevipolide M

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Abstract

The first stereoselective total synthesis of a cytotoxic brevipolide M, which shares a pyrone framework bearing a tetrahydrofuran moiety and a cinnamate group with the readily available (−)-DET, is described. The key steps involved in the synthesis are the epoxide-opening, Brown's allylation, and the RCM reaction to install an α,β-unsaturated lactone ring and the inversion of the C-6′ stereogenic hydroxyl group using the Mitsunobu reaction.

Graphical abstract: First stereoselective total synthesis of brevipolide M

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Publication details

The article was received on 14 Jun 2017, accepted on 12 Jul 2017 and first published on 12 Jul 2017


Article type: Paper
DOI: 10.1039/C7OB01438D
Citation: Org. Biomol. Chem., 2017,15, 6393-6400
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    First stereoselective total synthesis of brevipolide M

    K. Shiva Raju and G. Sabitha, Org. Biomol. Chem., 2017, 15, 6393
    DOI: 10.1039/C7OB01438D

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