Synthesis of a deoxyristomycinic acid derivative using organomanganese chemistry

Abstract

Coupling of (3-chloro-2-methylanisole) tricarbonylmanganese tetrafluoroborate with the phenoxide derived from methyl N-Boc-3-hydroxyphenylglycinate gave the diaryl ether manganese complex (6). This complex underwent regiospecific, stereoselective reaction with Schollkopf's chiral glycine enolate equivalent to give a mixture of dienyl-Mn(CO)₃ complexes that were converted in a two-step sequence into the protected deoxyristomycinic acid derivative (12).