We have previously reported development of biomimetic, asymmetric [3 + 2] photocycloadditions between 3-hydroxyflavones and cinnamate dipolarophiles to access (-)-rocaglamide and related natural products. This presentation will describe enantioselective syntheses of the cyclopenta[b,c]benzopyrans (+)-ponapensin and (+)-elliptifoline, antipodes of the natural products via photocycloaddition and further steps including diastereoselective nucleophilic addition to an acyliminium intermediate. These total syntheses elucidated the absolute configurations of both metabolites, allowed us to reassign the relative configuration of elliptifoline, and have led to interesting biosynthetic implications.

Total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline via enantioselective photocycloaddition of 3-hydroxyflavones and cinnamic esters

245th National Meeting (2013)

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