Synthetic studies of thiazoline and thiazolidine-containing natural products - 2. Total synthesis of the antimycoplasma antibiotic micacocidin

Article abstract of DOI:10.1016/S0040-4020(99)00583-9

Synthesis of the fight half of micacocodin (segment B) and subsequent completion of total synthesis of the antimycoplasma antibiotic micacocidin is described. The desired S-configuration at C-14 secondary carbinol was obtained by stereoselective reduction of the preceding ketone in accordance with the Cram rule. Condensation of two labile segments, A and B, was achieved in the presence of potassium acetate. The chiral center at C-10 was finally isomerized to the natural configuration through formation of the Zn complex.