Stereocontrolled semi-syntheses of deguelin and tephrosin

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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Veröffentlicht in:Organic & biomolecular chemistry 2017-02, Vol.15 (7), p.1593-1596
Hauptverfasser: Russell, David A, Freudenreich, Julien J, Ciardiello, Joe J, Sore, Hannah F, Spring, David R
Format: Artikel
Sprache:eng
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Molecular Conformation
Rotenone - analogs & derivatives
Rotenone - chemical synthesis
Rotenone - chemistry
Stereoisomerism
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container_issue 7
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container_title Organic & biomolecular chemistry
container_volume 15
creator Russell, David A
Freudenreich, Julien J
Ciardiello, Joe J
Sore, Hannah F
Spring, David R
description 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.
doi_str_mv 10.1039/c6ob02659a
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source MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection
subjects Molecular Conformation
Rotenone - analogs & derivatives
Rotenone - chemical synthesis
Rotenone - chemistry
Stereoisomerism
title Stereocontrolled semi-syntheses of deguelin and tephrosin
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