Synthesis of 11-cis-retinoids by hydrosilylation-protodesilylation of an 11,12-didehydro precursor: easy access to 11- and 12-mono- and 11,12-dideuteroretinoids.

Authors :: Bergueiro J
Montenegro J
Saá C
López S
Source :: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2012 Oct 29; Vol. 18 (44), pp. 14100-7. Date of Electronic Publication: 2012 Sep 20.
Publication Year :: 2012
Abstract: An expeditious, highly efficient approach to 11-cis-retinoids was achieved by semihydrogenation of a readily available 11-yne precursor through a hydrosilylation-protodesilylation protocol. The complete chemo-, regio-, and syn-stereoselectivity of the method also allowed direct access to 11- and 12-monodeutero-, and 11,12-dideutero-11-cis-retinoids. The analogous trans series was not accessible by this route, and was synthesized by means of Hiyama coupling.<br /> (Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Subjects :: Catalysis
Deuterium chemistry
Oxidation-Reduction
Platinum chemistry
Retinoids chemical synthesis
Ruthenium chemistry
Stereoisomerism
Retinoids chemistry
Silicon chemistry

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