Abstract
Addition of sulfur-stabilised carbanions to (–)-5-(1-menthyloxy)furan-2(5H)-one followed by reaction with an aromatic aldehyde affords a short synthesis of enantiomerically pure dibenzylbutyrolactone derivatives. Desulfurisation with NaBH4/NiCl2 proceeds in almost quantitative yield, and reduction with NaBH4/KOH gives the parent dibenzylbutyroactones including (–)-6-epi-podorhizol. These undergo cyclisation with acid to give homochiral aryltetralins including (–)-deoxyisopodophyllotoxin in high yield.
Published Version
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