Studies toward the total synthesis of (-)-zampanolide

ORGN 65

Dawn M. Troast, dtroast@chem.bu.edu, Department of Chemistry, Boston University, 590 Commonwealth Ave., Boston, MA 02215 and John A. Porco Jr., porco@bu.edu, Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215.
The unique 20-membered macrolide (-)-zampanolide was isolated in 1996 by Tanaka and Higa from the sponge Fasciospongia rimosa, collected near Okinawa, Japan. This structurally interesting molecule has a high degree of unsaturation and an unusual N-acyl hemiaminal side chain. In addition to its unique structure, zampanolide displays potent cytotoxic activity (1-5 ng/mL) against a number of tumor cell lines. In this presentation, we will review our recent progress towards (-)-zampanolide, which entails a one-pot reduction/vinylogous aldol reaction, an intramolecular silyl-modified Sakurai reaction, and macrocyclization employing a bis(allylstannane).

 

Total Synthesis of Complex Molecules
1:00 PM-5:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- 202B, Oral

Division of Organic Chemistry

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