Towards the synthesis of the furanosteroids

ORGN 752

E. Hampton Sessions Jr. and Peter A. Jacobi. Department of Chemistry, Dartmouth College, 6128 North College St, Burke Laboratory, Hanover, NH 03755
Furanosteroids (eg. Viridin and Wortmannin) are fungal metabolites possessing various biological activities, the most important being the inhibition of the phosphoinositide-3-kinases (PI3K). PI3K's are enzymes involved in important cellular processes such as adhesion, motility, proliferation and apoptosis. Our goal is to develop an efficient synthetic route to this class of natural products which could be modified to synthesize analogues with greater potency and specificity. The key step in our synthetic plan is an intramolecular Diels-Alder/ retro-Diels-Alder reaction between oxazoles and alkynes which produces highly substituted fused furans. Progress toward the synthesis of the furanosteroids will be presented.

 

Heterocycles and Aromatics
1:00 PM-5:00 PM, Thursday, 1 September 2005 Washington DC Convention Center -- Ballroom B, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005