Synthesis of (–)-Cytoxazone, a Novel Cytokine Modulator Isolated fromStreptomyces sp.

Abstract

Cytoxazone [(4R,5R)-(–)-5-hydroxymethyl-4-(4-methoxyphenyl)-2-oxazolidinone, 1], a new immunosuppressant, was synthesized by starting from p-methoxycinnamyl alcohol (2) employing the Sharpless asymmetric dihydroxylation as the key reaction in 26% overall yield (7 steps).