Toward Pluramycins with Epoxy Side Chain: Syntheses of Kidamycinone and Epoxykidamycinone (Saptomycinone H).

For exploring general routes to the pluramycin-class of antibiotics, including congeners with epoxide-bearing side chains, syntheses of kidamycinone and its epoxide (epoxykidamycinone) have been achieved. At the stage of the A-ring cyclization with alkene-bearing side chain, the desired 6-endo product was obtained as a major compound, although the corresponding undesired 5-exo product was also formed.