The first total synthesis of a type II manumycin antibiotic, (+)-TMC-1 A: the total syntheses of (–)-LL-C10037β and (+)-manumycin B

Abstract

A procedure using Na[PhSeB(OEt)₃] is reported for conversion of the type I epoxy ketone manumycins into the type II β-hydroxyketone variants; using this procedure, (–)-LL-C10037β and (+)-TMC-1A have been prepared for the first time; the first synthesis of (+)-manumycin B, which provides full stereochemical clarification of the natural product, is also described.