Stereocontrolled semi-syntheses of deguelin and tephrosinElectronic supplementary information (ESI) available: 1H and 13C NMR spectra. See DOI: 10.1039/c6ob02659a

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 conversi...

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Bibliographic Details
Main Authors: Russell, David A, Freudenreich, Julien J, Ciardiello, Joe J, Sore, Hannah F, Spring, David R
Format: Article
Language:English
Online Access:Get full text
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Summary: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. We describe stereocontrolled semi-syntheses of deguelin and tephrosin, anti-cancer rotenoids isolated from Tephrosia vogelii .
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02659a