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Synfacts 2007(1): 0001-0001  
DOI: 10.1055/s-2006-955651
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of the α-C-Glycoside Analogue of KRN7000

Contributor(s): Philip Kocienski
P. Wipf*, J. G. Pierce
University of Pittsburgh, USA
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

The α-C-glycoside analogue of KRN7000 is 102-103 more potent than KRN7000 in T-cell suppression of melanoma and malaria models. Key steps in the synthesis are (a) the highly stereoselective addition of an alkenylalane to an N-tert-butanesulfinyl imine (C to D) and (b) the diastereoselective epoxidation of the Boc imide E leading to H.