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

Synthesis of the right half of micacocodin (segment B) and subsequent compl etion of total synthesis of the antimycoplasma antibiotic micacocidin is de scribed. The desired S-configuration at C-14 secondary carbinol was obtaine d by stereoselective reduction of the preceding ketone in accordance with t he 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 i somerized to the natural configuration through formation of the Zn complex. (C) 1999 Elsevier Science Ltd. All rights reserved.