Planta Med 2013; 79 - CL19
DOI: 10.1055/s-0033-1348544

Toward the Total Synthesis of Luminamicin, a Specific Anti-Anaerobic Bacteriacide

A Sugawara 1, A Kimishima 1, H Takada 1, T Hirose 1, T Matsumaru 1, S Ōmura 1, T Sunazuka 1
  • 1Kitasato Institute for Life Sciences and Graduate School of Infection Control Sciences, Kitasato University, 5 – 9-1 Shirokane, Minato-ku, Tokyo, 108 – 8641, Japan

Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. It contains a highly functionalized 11-oxatricyclo[,703,8]undecane, associated with a 10-membered macrolactone moiety which possesses a (E)-trisubstituted olefin and a 14-membered macrolactone, with an enol ether conjugated with a maleic anhydride functionality. Due to its intriguing structure and interesting biological activity, we have been focusing on its total synthesis. We synthesized the key intermediate (2) from the vinyltin (4) via hydrostannylation/Stille reaction and the framework of 3 from the unsaturated aldehyde (5) via intramolecular 1,6-oxa-Michael reaction. In this meeting, progress toward the total synthesis of 1 will be presented in detail.