The first total synthesis of a type II manumycin antibiotic, (+)-TMC-1A: the total syntheses of (-)-LL-C10037 beta and (+)-manumycin B

A procedure using Na[PhSeB(OEt)(3)] is reported for conversion of the type I epoxy ketone manumycins into the type II beta-hydroxyketone variants; usi ng this procedure, (-)-LL-C10037 beta 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.