Highly convergent enantioselective formal total synthesis of leucascandrolide A

ORGN 692

William J. Andrews, wjandrew@indiana.edu and P. Andrew Evans. Department of Chemistry, Indiana University, 800 E. Kirkwood, Bloomington, IN 47405
Leucascandrolide A, isolated from the calcareous sponge Leucascandra caveolata, displays potent in vitro cytotoxic activity against KB and P388 tumor cell lines in addition to antifungal activity inhibiting the growth of Candida albicans. We have developed a highly convergent synthetic strategy that will allow for the most expeditious total synthesis of this biologically important and structurally appealing natural product developed to date. The key step in this synthesis involves sequential bismuth-mediated etherification reactions for the one-pot synthesis of the bis-tetrahydropyran core.

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Wednesday, 13 September 2006 Moscone Center -- Room 132, Oral

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006