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Synfacts 2005(3): 0312-0312  
DOI: 10.1055/s-2005-916138
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (-)-Colchicine via a Rh-Triggered Cycloaddition Cascade

Contributor(s): Mark Lautens, Josephine Yuen
T. Graening, V. Bette, J. Neudörfl, J. Lex, H.-G. Schmalz*
Universität zu Köln, Germany
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

The Rh-catalyzed domino reaction of an α-diazoketone into an oxatetracyclic intermediate via a [3+2] cycloaddition of an in situ generated carbonyl ylide is described. The key intermediate was used to synthesize enantiopure
(-)-colchicine and (-)-isocolchicine. The reaction proceeded with complete diastereoselectivity.