Stereoselective synthesis of functionalized trisubstituted olefins via palladium(0)-catalyzed cross-coupling reaction.

Arefolov, A; Langille, N F; Panek, J S

Arefolov, A; Langille, N F; Panek, J S.

Afiliación

Arefolov A; Department of Chemistry and Center for Streamlined Synthesis, Metcalf Center for Science and Engineering, 590 Commonwealth Avenue, Boston University, Boston, Massachusetts 02215, USA.

Org Lett ; 3(21): 3281-4, 2001 Oct 18.

Article en En | MEDLINE | ID: mdl-11594814

RESUMEN

[reaction: see text]. A highly flexible and stereoselective protocol for the synthesis of branched (E)- and (Z)-trisubstituted alkenes has been developed. The key steps are hydrozirconation-iodination of (1-alkynyl)trimethylsilane followed by Negishi-type cross-coupling. The resultant (Z)-vinyl silane is iododesilylated and subjected to a second cross-coupling reaction to give the trisubstituted olefin. Model studies aimed at the construction of the C14-C15 (Z)-trisubstituted olefin of discodermolide and the C8-C9 (Z)-trisubstituted olefin of callystatin A and analogues are also described.

Asunto(s)

Alcanos; Alquenos/síntesis química; Carbamatos; Catálisis; Ácidos Grasos Insaturados/síntesis química; Yodo; Lactonas/síntesis química; Modelos Moleculares; Paladio/química; Pironas; Silanos; Estereoisomerismo; Circonio

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Carbamatos / Alcanos / Alquenos Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2001 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos

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