Studies in mycological chemistry. Part XX. Synthesis of (±)-tetrahydro-4-hydroxy-6-methoxyfuro[2,3-b]benzofuran, a racemic form of a laevorotatory degradation product of dihydrosterigmatocystin

Abstract

A synthesis of (±)-2,3,3a,8a-tetrahydro-4-hydroxy-6-methoxyfuro[2,3-b]benzofuran is described. Spectroscopic comparison of this material with a laevorotatory compound formed by degradation of the dihydro-derivative of sterigmatocystin (a metabolite of Aspergillus versicolor) has confirmed the structure of the degradation product.