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Synfacts 2007(1): 0007-0007  
DOI: 10.1055/s-2006-955649
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Rhazinilam

Contributor(s): Philip Kocienski
Z. Liu, A. S. Wasmuth, S. G. Nelson*
University of Pittsburgh, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

Rhazinilam interferes with tubulin polymerization. The present synthesis proceeds in 22% overall yield (16 steps) from aldehyde A. Key steps include (a) an asymmetric [2+2] cycloaddition used to generate B and (b) a Au(I)-catalyzed cyclization of the scalemic allene C.