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Synfacts 2009(8): 0817-0817  
DOI: 10.1055/s-0029-1217578
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Quebrachamine

Contributor(s): Philip Kocienski, Stewart Eccles
E. S. Sattely, S. J. Meek, S. J. Malcolmson, R. R. Schrock, A. H. Hoveyda*
Boston College, Chestnut Hill and, Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

Quebrachamine is an Aspidosperma alkaloid that is an adrenergic blocker. This synthesis is noteworthy for the highly enantioselective ring-closing cross-metathesis (G → I) using a chiral molybdenum catalyst which is stereogenic at the metal center.