A stereocontrolled approach for the synthesis of 2,5-diaryl-3,4-disubstituted furano lignans through a highly diastereoselective aldol condensation of an ester enolate with an α-chiral center: total syntheses of (−)-talaumidin and (−)-virgatusin

Artigo Revisado por pares

A stereocontrolled approach for the synthesis of 2,5-diaryl-3,4-disubstituted furano lignans through a highly diastereoselective aldol condensation of an ester enolate with an α-chiral center: total syntheses of (−)-talaumidin and (−)-virgatusin

2008; Elsevier BV; Volume: 49; Issue: 21 Linguagem: Inglês

10.1016/j.tetlet.2008.03.105

ISSN

1873-3581

Autores

Kiran Matcha, Subrata Ghosh,

Tópico(s)

Carbohydrate Chemistry and Synthesis

Resumo

A general stereocontrolled approach for entry into a family of highly biologically active 2,5-diaryl-3,4-disubstituted furano lignans has been developed. The key step involves a diastereoselective aldol-type condensation of an ester enolate having an α-chiral center with an aromatic aldehyde. The methodology has been illustrated with the total syntheses of (−)-talaumidin and (−)-virgatusin.

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A stereocontrolled approach for the synthesis of 2,5-diaryl-3,4-disubstituted furano lignans through a highly diastereoselective aldol condensation of an ester enolate with an α-chiral center: total syntheses of (−)-talaumidin and (−)-virgatusin