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Synfacts 2007(4): 0349-0349  
DOI: 10.1055/s-2007-968290
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Phaseolinic Acid

Contributor(s): Philip Kocienski
G. P. Howell, S. P. Fletcher, K. Geurts, B. ter Horst, B. L. Feringa*
University of Groningen, The Netherlands
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

The synthesis of (-)-phaseolinic acid exemplifies a procedure for the Cu(I)-catalyzed asymmetric 1,4-addition of Grignard reagents to α,β-unsaturated thioesters followed by aldol reaction of the resultant magnesium enolates with aldehydes to give syn,syn-stereotriads with excellent diastereo- and enantioselectivity. The method is a rare example of the asymmetric conjugate addition of an organometallic reagent to an acyclic α,β-unsaturated carbonyl derivative.