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Synfacts 2008(9): 0943-0943  
DOI: 10.1055/s-2008-1078647
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Application of Asymmetric [3+2] Cycloaddition

Contributor(s): Mark Lautens, Frédéric Ménard
K. Tran, P. J. Lombardi, J. L. Leighton*
Columbia University, New York, USA
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Publication History

Publication Date:
22 August 2008 (online)

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Significance

The total synthesis of manzacidin A was accomplished in only six steps, with an overall yield of 26%. It demonstrated the impressive usefulness of a methodology previously developed by the authors (J. Am. Chem. Soc. 2005, 127, 9974). The key step served to install both stereocenters of the target molecule in one operation with excellent enantioselectivity. Previous syntheses of manzacidins installed the stereocenters sequentially and led to diastereomeric mixtures.