Elsevier

Tetrahedron

Volume 48, Issue 23, 5 June 1992, Pages 4757-4766
Tetrahedron

Synthesis of (+)-8-methyl cercosporamide: Stereochemical correlation of natural (−)-cercosporamide with (+)-usnic acid

Dedicated to Professor Gabor Fodor on the occasion of his 75th birthday.
https://doi.org/10.1016/S0040-4020(01)81572-6Get rights and content

Abstract

The absolute configuration of the antifungal antibiotic cercosporamide was established as C-9b-(−)-(S) by correlation with synthetic (+)-8-methylcercosporamide. This was accomplished via conversion of the isoxazole (6) available from (+)-usnic acid. Structure revision of the key isoxazole (6), previously assigned structure (5), is described; some of the 13C-assignments for usnic acid made by previous workers have also been corrected.

Synthesis of (+)-8-methyl cercosporamide from (+)-usnic acid is described and the absolute configuration of cercosporamide established as C-9b-(−)-(s).

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