Total Synthesis of Sclerotinin A

Abstract

Sclerotinin A (3, 6, 8-trihydroxy-3, 4, 5, 7-tetramethyl-3, 4-dihyroisocoumarin: 1), a metabolite of Scierotinia sclerotiorum, was first totally synthesized. The pentenone ring of 2, 3, 4, 6-tetramethyl-5, 7-dimethoxyindanone (VII_a) which was obtained from 2, 4-dimethylresorcinol dimethyl ether (VI) through a new synthetic process, was cleavaged oxidatively, and demethylated to I. Sclerotinin A was also yielded from indanone dibenzyl ether (VII_b) by the same method and reductive debenzylation.