Access to lincomycin N-oxide isomers controlled by reaction conditions

Pospíšil, Stanislav; Sedmera, Petr; Halada, Petr; Havlíček, Libor; Spížek, Jaroslav
TETRAHEDRON LETTERS 45: 2943-2945, 2004

Keywords: lincomycin oxidation; hydrogen peroxide; alkaline
Abstract: Oxidation of lincomycin with H2O2 in alkaline media leads to N-oxides, besides the conversion of thiomethyl group into sulfoxides and sulfones. NH4OH favors formation of the S-isomer; both R- and S-iosmers of the N-oxide are formed in the presence of NaOH. Addition of acetonitrile markedly accelerates the reaction.
IEB authors: Libor Havlíček