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Synfacts 2008(10): 1009-1009
DOI: 10.1055/s-2008-1078284
DOI: 10.1055/s-2008-1078284
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Callipeltoside C
Contributor(s):Phiip KocienskiJ. 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
Princeton University and Caltech, Pasadena, USA
Total Synthesis and Structural Revision of Callipeltoside C
Angew. Chem. Int. Ed. 2008, 47: 3568-3572
Further Information
Publication History
Publication Date:
22 September 2008 (online)
Key words
callipeltoside C - organocatalysis - aldols - α-oxyamination - palladium
Significance
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.
Comment
This first synthesis of callipeltoside C established the correct absolute stereochemistry of the pendent 2-O-methylevalose (N).