Stereocontrolled semi-syntheses of deguelin and tephrosin.
Accepted version
Peer-reviewed
Repository URI
Repository DOI
Change log
Authors
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.
Description
Keywords
Journal Title
Org Biomol Chem
Conference Name
Journal ISSN
1477-0520
1477-0539
1477-0539
Volume Title
15
Publisher
Royal Society of Chemistry (RSC)
Publisher DOI
Rights and licensing
Except where otherwised noted, this item's license is described as Attribution 4.0 International
Sponsorship
Engineering and Physical Sciences Research Council (EP/J016012/1)
European Research Council (279337)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
European Research Council (279337)
Engineering and Physical Sciences Research Council (EP/K039520/1)
Engineering and Physical Sciences Research Council (EP/P020291/1)
Our research is supported by the EPSRC, BBSRC, MRC, Wellcome Trust and ERC (FP7/2007–2013; 279337/DOS). D. A. R thanks Cancer Research UK for funding. D. R. S. acknowledges support from a Royal Society Wolfson Research Merit award.