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Synfacts 2007(3): 0231-0231  
DOI: 10.1055/s-2007-968191
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Secramine A

Contributor(s): Philip Kocienski
B. Xu, H. Pelish, T. Kirchhausen, G. H. Hammond*
University of Louisville and Harvard Medical School, Boston, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

Secramine A was discovered by Shair and co-workers (J. Am. Chem. Soc. 2001, 123, 6740-6741) from a library of 2,500 analogues of the alkaloid galanthamine. It inhibits activation of Cdc42, a Rho GTPase inhibitor that activates actin polymerization. The key step in the synthesis of Hammond and co-workers is an oxidative phenolic coupling of the tyrosine derivative C leading to the spirocyclohexadienone D.