Revised Structure of Gonioheptolide A

Abstract

(±)-Gonioheptolide A (3) was unambiguously synthesized from (±)-goniofupyrone (4) and thereby its structure was revised as (1'R^*, 2S^*, 3S^*, 4S^*, 5R^*)-3, 4-dihydroxy-2-[(1'-hydroxy-2'-methoxycarbonyl)ethyl]-5-phenyl-tetrahydrofuran. Methanolysis of (±)-goniofupyrone (4) with conc.H₂SO₄ at room temperature provided (±)-gonioheptolide A (3) in 48% yield. The synthetic (±)-gonioheptolide A and its triacetate were comparable to natural gonioheptolide A and its triacetate, respectively.