SULFOGRISEOFULVIN DERIVATIVES - SYNTHESIS BY [4-STRUCTURE ANALYSIS, AND ANTIFUNGAL ACTIVITY OF PIRO[1,3-BENZOXATHIOLE-2,1'-CYCLOHEX-2'-EN]-4'-ONE 3,3-DIOXIDES(2]CYCLOADDITION, STRUCTURE, PROPERTIES, CRYSTAL)

Syntheses of substituted, especially of fluoro, substituted benzoxathi ole 1,1-dioxides, are described. These derivatives were transformed vi a the Peterson olefination into substituted 2-alkylidene derivatives 2 7. Diels-Alder reactions of 27 with 1,1-dimethoxy- and 1-methoxy-3-tri methylsiloxy-1,3-butadiene (30, 32) gave sulfone analogues 31 of grise ofulvin (named sulfogriseofulvins). From F-27, a number of cis-isomers with the relative stereochemistry of griseofulvin (cis-31) was prepar ed, and from E-isomers of 27, compounds (trans-31) with relative stere ochemistry of epigriseofulvin were obtained. Some related compounds (3 3, 38) are synthesized by slight modifications. The stereochemistry is established by spectroscopic methods and crystal structure analyses. The compounds 31 were tested against three species of dermatophytes. T he biological activities were all significantly: lower than that of gr iseofulvin.