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Issue 7, 2017
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Stereocontrolled semi-syntheses of deguelin and tephrosin

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Abstract

We describe stereocontrolled semi-syntheses of deguelin and tephrosin, anti-cancer rotenoids isolated from Tephrosia vogelii. Firstly, we present a new two-step transformation of rotenone into rot-2′-enonic acid via a zinc-mediated ring opening of rotenone hydrobromide. Secondly, following conversion of rot-2′-enonic acid into deguelin, a chromium-mediated hydroxylation provides tephrosin as a single diastereoisomer. An Étard-like reaction mechanism is proposed to account for the stereochemical outcome. Our syntheses of deguelin and tephrosin are operationally simple, scalable and high yielding, offering considerable advantages over previous methods.

Graphical abstract: Stereocontrolled semi-syntheses of deguelin and tephrosin

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Publication details

The article was received on 05 Dec 2016, accepted on 24 Jan 2017 and first published on 24 Jan 2017


Article type: Communication
DOI: 10.1039/C6OB02659A
Citation: Org. Biomol. Chem., 2017,15, 1593-1596
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    Stereocontrolled semi-syntheses of deguelin and tephrosin

    D. A. Russell, J. J. Freudenreich, J. J. Ciardiello, H. F. Sore and D. R. Spring, Org. Biomol. Chem., 2017, 15, 1593
    DOI: 10.1039/C6OB02659A

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