Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (–)-anisomycin and (+)-polyoxamic acid

Abstract

Intramolecular iodoamidation of pentenetriol 2 provides trihydroxy carbamate 8 in 94% de and was elaborated to (–)-anisomycin 15 and (+)-polyoxamic acid 19.