Download PDF
Synfacts 2007(9): 0893-0893  
DOI: 10.1055/s-2007-968828
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Terpestacin

Contributor(s): Philip Kocienski
B. M. Trost*, G. Dong, J. A. Vance
Stanford University, USA
Further Information

Publication History

Publication Date:
23 August 2007 (online)

    Permissions and Reprints

Significance

Terpestacin inhibits (a) formation of syncytia by HIV-infected T cells and (b) angiogenesis. Trost and co-workers make very effective use of α-diketone chemistry to create three C-C bonds. Highly selective Pd-catalyzed asymmetric allylic alkylation reactions of an α-diketone (A to C and H to I) generate allylic ethers which are heated under microwave conditions to effect a Claisen rearrangement.