Stereoselective Synthesis of Trienoic Acids: Synthesis of Retinoic Acids and Analogues

Mohamed Abarbri; Jean-Luc Parrain; Alain Duchêne; Jérôme Thibonnet

doi:10.1055/s-2006-950201

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Synthesis 2006(17): 2951-2970
DOI: 10.1055/s-2006-950201

FEATUREARTICLE

Stereoselective Synthesis of Trienoic Acids: Synthesis of Retinoic Acids and Analogues

Mohamed Abarbri^a, Jean-Luc Parrain^b, Alain Duchêne^a, Jérôme Thibonnet*^a
^a Laboratoire de Synthèse et Physicochimie Organique et Thérapeutique, EA 3857, Faculté des Sciences de Tours, Parc de Grandmont, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: jerome.thibonnet@univ-tours.fr;
^b Laboratoire de Synthèse par Voie Organométallique, UMR CNRS 6178, Case postale D12, Faculté des Sciences de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Further Information

Publication History

Received 13 January 2006
Publication Date:
15 August 2006 (online)

Abstract
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Abstract

Stereoselective construction of conjugated trienoic acids was achieved through two successive Stille reactions, the first step consisting of the coupling of (E)-1,2-bis(tributylstannyl)ethene and tributylstannyl (Z)- or (E)-3-iodoalk-2-enoates. Two different routes were used for the second step: (1) cross-coupling of the stannyldienoic acid reagents and vinyl iodides, or (2) cross-coupling of vinylstannane reagents and the tributylstannyl 5-iodopenta-2,4-dienoates generated by iododestannylation of stannyldienes. Vinylstannanes synthesized by stannylmetalation of the Negishi dienyne derived from β- or α-ionone and safranal thus provided access to stereodefined retinoic acids. Some retinoid and yne analogues were also prepared by Sonogashira coupling.

Key words

Stille reaction - cross-coupling - tin compounds - trienoic acids - retinoic acids - polyenic acids

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2

The traditional retinoid numbering system was used in the text when all-trans-retinoic acid was referred to. The IUPAC nomenclature was used in the experimental section.

33

Compounds 7 are purified by column chromatography on reversed-phase C18 silica gel.