Stereocontrolled semi-syntheses of deguelin and tephrosin

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 conv...

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Published inOrganic & biomolecular chemistry Vol. 15; no. 7; pp. 1593 - 1596
Main Authors Russell, David A., Freudenreich, Julien J., Ciardiello, Joe J., Sore, Hannah F., Spring, David R.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.02.2017
Subjects
Chemistry
Chemistry, Organic
Molecular Conformation
Physical Sciences
Rotenone - analogs & derivatives
Rotenone - chemical synthesis
Rotenone - chemistry
Science & Technology
Stereoisomerism
(+/-)-DEGUELIN
ACID
ROTENOIDS
STEREOCHEMISTRY
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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 Etard-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.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02659a