Synthesis of elemane bis-lactones structurally related to vernolepin

Article abstract of DOI:10.1016/S0040-4039(98)00363-3

The chemical transformation of santonin into an elemane bis-lactone structurally related to the antitumour compound vernolepin is reported. The transformation of ring A of santonin into a hemiacetal δ-lactone was achieved in eleven steps. The spectroscopic characteristics of the synthetic product obtained in this way revealed that the proposed structure for the natural product should be revised.