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Synthesis 2006(17): 2951-2970
DOI: 10.1055/s-2006-950201
DOI: 10.1055/s-2006-950201
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New YorkStereoselective Synthesis of Trienoic Acids: Synthesis of Retinoic Acids and Analogues
Further Information
Received
13 January 2006
Publication Date:
15 August 2006 (online)
Publication History
Publication Date:
15 August 2006 (online)
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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References
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.
33Compounds 7 are purified by column chromatography on reversed-phase C18 silica gel.