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

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...

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Veröffentlicht in:Synthesis (Stuttgart) 2006-09, Vol.2006 (17), p.2951-2970
Hauptverfasser: Abarbri, Mohamed, Parrain, Jean-Luc, Duchêne, Alain, Thibonnet, Jérôme
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Sprache:eng
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Zusammenfassung: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950201