Synthesis and structure revision of wasulfisides: glucosyl disulfides isolated from wasabi

Abstract

The first syntheses of three natural glucosyl disulfides—wasulfisides A, B, and 3-epi-wasulfiside B—were successfully accomplished. These compounds were originally isolated from wasabi (Eutrema japonicum) and possess a rare natural β-glucosyl disulfide motif. The core structure was efficiently constructed via S–S bond formation between a β-glucosyl thiotosylate and various thiols. The overall yields reached 37%, starting from d-glucose. Accordingly, the structure of wasulfiside A, a unique oxadithiocine-containing compound, was successfully revised based on the syntheses of its regio- and stereoisomers.