Download PDF
Synfacts 2006(2): 0098-0098  
DOI: 10.1055/s-2005-921780
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Lithospermic Acid

Contributor(s): Philip Kocienski
S. J. O’Malley, K. L. Tan, A. Watzke, R. G. Bergman*, J. A. Ellman*
University of California at Berkeley, USA
Further Information

Publication History

Publication Date:
23 January 2006 (online)

    Permissions and Reprints

Significance

The first synthesis of (+)-Lithospermic acid, a nontoxic inhibitor of HIV-1 integrase, was achieved using an asymmetric intramolecular alkylation of A via rhodium-catalyzed C-H bond activation to give dihydrobenzofuran B in 88% yield (er = 86:14). This is the first example of chiral imine-directed C-H bond activation.