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Synfacts 2008(8): 0793-0793  
DOI: 10.1055/s-2008-1078537
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Yohimbine

Contributor(s): Philip Kocienski, Stewart Eccles
D. J. Mergott, S. J. Zuend, E. N. Jacobsen*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

A very concise synthesis of (+)-yohimbine features creation of the single stereogenic center at C3 in tetrahydro-β-carboline D via an organocatalytic asymmetric Pictet-Spengler reaction. This stereogenic center then controls the simultaneous formation of rings D and E as well as four contiguous stereogenic centers by an intramolecular Diels-Alder annulation (G → I).