Synthesis of (±)-(4aα, 6α, 7α, 7aα)-Hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-3(1H)-one, a Structure Common to Abelialactone, Aglykon A1, and Isoboonein

Abstract

Synthesis of (±)-(4aα, 6α, 7α, 7aα)-hexahydro-6-hydroxy-7-methylcyclopenta[c]pyran-3(1H)-one [(±)-1] has been achieved through an 8-step route starting from 6, 7-dihydrocyclopenta-1, 3-dioxin-5(4H)-one (4). The identities of synthetic (±)-1 with abelialactone, Aglykon A1, and isoboonein permitted the unequivocal assignment of this common structure and the relative stereochemistry to these cyclopentano-monoterpene lactones.