title: 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.
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.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, Spain.
authors.forename: Julián
authors.initials: J
authors.lastname: Bergueiro
authors.forename: Javier
authors.initials: J
authors.lastname: Montenegro
authors.forename: Carlos
authors.initials: C
authors.lastname: Saá
authors.forename: Susana
authors.initials: S
authors.lastname: López
mesh_terms: D002384:Catalysis; D003903:Deuterium / Q000737:chemistry; D010084:Oxidation-Reduction; D010984:Platinum / Q000737:chemistry; D012176:Retinoids / Q000138:chemical synthesis / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D012176:Retinoids; D010984:Platinum; D012428:Ruthenium; D003903:Deuterium; D012825:Silicon