Synthesis of Callipeltoside C

doi:10.1055/s-2008-1078284

Synfacts 2008(10): 1009-1009
DOI: 10.1055/s-2008-1078284

Synthesis of Natural Products and Potential Drugs

Synthesis of Callipeltoside C

Rezensent(en):Phiip Kocienski

J. Carpenter, A. B. Northrup, D. Chung, J. J. M. Weiner, S.-G. Kim, D. W. C. MacMillan*
Princeton University and Caltech, Pasadena, USA
Total Synthesis and Structural Revision of Callipeltoside C
Angew. Chem. Int. Ed. 2008, 47: 3568-3572

Abstract

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Key words

callipeltoside C - organocatalysis - aldols - α-oxyamination - palladium

Significance

<P>Proline catalysis of two directed aldol reactions and an α-oxyamination reaction are salient features of a very concise and efficient synthesis of callipeltoside C.</P>

Comment

<P>This first synthesis of callipeltoside C established the correct absolute stereochemistry of the pendent 2-O-methylevalose (N).</P>

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