Synlett 2016; 27(07): 1077-1082
DOI: 10.1055/s-0035-1561340
letter
© Georg Thieme Verlag Stuttgart · New York

Highly Diastereoselective 1,6-Conjugate Addition of Arylboronic Acids to Securinine

Marc Perez
a   PSL Research University, Chimie ParisTech – CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France   eMail: virginie.vidal@chimie-paristech.fr
,
Tahar Ayad
a   PSL Research University, Chimie ParisTech – CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France   eMail: virginie.vidal@chimie-paristech.fr
,
Philippe Maillos
b   Institut de Recherche Pierre Fabre, 81600 Gaillac, France
,
Valérie Poughon
c   Unité de Service et de Recherche CNRS, Pierre Fabre n°3388 ETaC CRDPF, 31035 Toulouse, France   eMail: jacques.fahy@pierre-fabre.com
,
Jacques Fahy*
c   Unité de Service et de Recherche CNRS, Pierre Fabre n°3388 ETaC CRDPF, 31035 Toulouse, France   eMail: jacques.fahy@pierre-fabre.com
,
Virginie Ratovelomanana-Vidal*
a   PSL Research University, Chimie ParisTech – CNRS, Institut de Recherche de Chimie Paris, 75005 Paris, France   eMail: virginie.vidal@chimie-paristech.fr
› Institutsangaben
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Publikationsverlauf

Received: 30. November 2015

Accepted after revision: 30. Dezember 2015

Publikationsdatum:
21. Januar 2016 (online)


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Abstract

The asymmetric 1,6-conjugate addition of arylboronic acids to natural securinine under rhodium(I) catalysis displays a very high regioselectivity, along with a remarkable diastereoselectivity (>99:1) and high yields. The in vitro cytotoxicity of the resulting securinine analogues was assayed against HCT-116 colon cancer cells, giving a new insight into the structure–activity relationship of securinine.