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Synthesis 2015; 47(22): 3513-3521
DOI: 10.1055/s-0034-1378812
DOI: 10.1055/s-0034-1378812
paper
Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans
Further Information
Publication History
Received: 25 May 2015
Accepted after revision: 14 June 2015
Publication Date:
12 August 2015 (online)
Abstract
Plant products (+)-sesamin, (+)-sesaminol, (+)-methylpiperitol, (+)-aschantin, and (+)-5'-hydroxymethylpiperitol were synthesized in a highly stereocontrolled manner through l-proline-catalyzed bifunctional-urea-accelerated cross-aldol reaction, followed by biomimetic construction of the furofuran lignan skeleton through a quinomethide intermediate.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378812.
- Supporting Information
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For general reviews on lignans, see:
For our investigations on probe molecules, see:
For selected examples:
For a short review, see:
See also:
Hajra and co-workers reported a similar aldol reaction, but they noted that reactions with electron-rich benzaldehydes were difficult, see:
For protection of phenols, see references 7d and 7e. For reviews on Ns chemistry, see: