Abstract
Abstract A novel and stereocontrolled process is described for the asymmetric synthesis of the tetrahydrofuran segment of a 2,3-dicarboxy-6,7-dihydroxy-1-(3′,4′-dihydroxyphenyl)-1,2- dihydronaphthalene mono-ester, trilobatin B, a lignan from the liverwort Bazzania trilobata . The key cis -substituted lactone ring was constructed in a stereoselective manner by Horner–Emmons reaction followed by the subsequent tandem Michael addition and cyclization of two types of lactol intermediates elaborated from natural sources.
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