A new method for the enantioselective synthesis of gamma,delta-disubstituted beta-hydroxy delta-lactones (5,6-dialkyl-5,6-dihydropyran-2-ones) is reported and exemplified for (+)-prelactone B and its C-4 epimer. Our approach is based on the ring-enlargement of suitably functionalized optically pure 4-hydroxycyclopentanones, which are readily obtained from chiral 4-hydroxycyclopent-2-enones derived from furans. The procedure is amenable to the large-scale synthesis of the title compounds.
Enantioselective synthesis of gamma,delta-disubstituted beta-hydroxy delta-lactones from furans: Synthesis of (+)-prelactone B and its C-4 epimer
MBA BLAZQUEZ, MIRIAM;
2003
Abstract
A new method for the enantioselective synthesis of gamma,delta-disubstituted beta-hydroxy delta-lactones (5,6-dialkyl-5,6-dihydropyran-2-ones) is reported and exemplified for (+)-prelactone B and its C-4 epimer. Our approach is based on the ring-enlargement of suitably functionalized optically pure 4-hydroxycyclopentanones, which are readily obtained from chiral 4-hydroxycyclopent-2-enones derived from furans. The procedure is amenable to the large-scale synthesis of the title compounds.
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