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Synfacts 2007(1): 0002-0002  
DOI: 10.1055/s-2006-955658
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Deoxyharringtonine

Contributor(s): Philip Kocienski, Thomas Snaddon
J. D. Eckelbarger, J. T. Wilmot, D. Y. Gin*
University of Illinois, Urbana, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The Cephalotaxus ester (-)-deoxyharringtonine displays potent activity against various leukemia cell lines. This synthesis is noteworthy for (1) the preparation of the benzazepine system by Cope rearrangement of an N-vinyl-2-aziridine, and (2) the installation of the spiro-fused pyrrolidine system by 1,3-dipolar cycloaddition of an azomethine ylide with phenyl vinyl sulfone. Facile acylation of the hindered C3-hydroxyl group has been achieved using the Yamaguchi anhydride (see Yamaguchi and co-workers Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993).