Planta Med 2012; 78 - PI20
DOI: 10.1055/s-0032-1320707

Total synthesis of (-)-Irciniastatin B

C An 1, AT Hoye 1, AB Smith III 1
  • 1Department of Chemistry, Laboratory for the Research on the Structure of Matter, and Monell Chemical Senses Center. University of Pennsylvania, Philadelphia, Pennsylvania 19104

(-)-Irciniastatin B, a novel cytotoxin with potent anticancer activity, was isolated from marine sponge Ircinia ramosa. Studies towards the total synthesis were initially based on our previously published synthesis of (+)-irciniastatin A [Smith, A. B.; et al. Org. Lett. 2008, 10, 5625]. The earlier route, employing phenolic SEM-ether as a protecting group proved too labile during the new multiple step synthetic sequence. A revised strategy employing the more robust 3,4-dimethoxybenzyl ethers now permits access to advanced intermediates. Studies directed towards the completion of (-)-irciniastatin B will be presented.