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Synfacts 2006(5): 0411-0411  
DOI: 10.1055/s-2006-934399
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Quinocarcin

Contributor(s): Philip Kocienski, John Cooksey
S. Kwon, A. G. Myers*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

The Myers group used a cascade of cyclization reactions to construct the tetracyclic ring system and three of the six stereocenters present in (-)-Quinocarcin - a pentacyclic alkaloid with antiproliferative biological activity. The role of the α-amino nitrile function as a latent electrophilic imine in the formation of rings C, D and E is especially noteworthy.