Stereocontrolled Total Syntheses of Optically Active Furofuran Lignans

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.

Key words

aldol reaction - natural products - organocatalysts - proline - stereoselective synthesis

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