ORGN 644

Studies toward the total synthesis of mycolactones A and B

Ning Yin, nyin@purdue.edu, Guangwei Wang, wang47@purdue.edu, and Ei-ichi Negishi, negishi@purdue.edu. Herbert C. Brown Laboratories of Chemistry, Purdue University, West Lafayette, IN 47907-2084

First isolated in 1999 from pathogen Mycobacterium ulcerans, mycolactones A and B (1) represent a novel class of polyketide macrolides displaying highly potent apoptotic activities. The side-chains of mycolactones A and B, that are protected as a MOM ether at C12 and TBS derivatives at C13 and C15 (2), were synthesized with a high degree of stereoselectivity. Our strategy is highlighted by using stepwise double substitution of 1,1-dibromo-1-alkenes and Pd-catalyzed cross-coupling as key steps. The preparation of the macrolide core is underway, and recent progress towards the total synthesis of mycolactones A and B will also be presented.

Total Synthesis of Complex Molecules
8:00 AM-12:00 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