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

Matcha, Kiran ; Ghosh, Subrata (2008) 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 Tetrahedron Letters, 49 (21). pp. 3433-3436. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/j.tetlet.2008.03.105

Abstract

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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Aldol Reaction; Enantiospecific; Lignans; Stereocontrol
ID Code:12379
Deposited On:10 Nov 2010 06:19
Last Modified:12 Feb 2011 11:05

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