Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable Schmidt donor of L-kedarosamine

Ohashi, Isao and Lear, Martin J. and Yoshimura, Fumihiko and Hirama, Masahiro (2004) Use of polystyrene-supported DBU in the synthesis and α-selective glycosylation study of the unstable Schmidt donor of L-kedarosamine. Organic Letters, 6 (5). pp. 719-722. ISSN 1523-7060

Full content URL: http://dx.doi.org/10.1021/ol036353v

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Use-of-polystyrene-supported-DBU-in-the-synthesis-and--selective-glycosylation-study-of-the-unstable-schmidt-donor-of-L-kedarosamine_2004_Organic-Letters.pdf

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Abstract

In the alpha-glycosylation study of the unusual, 2-deoxy amino sugar of kedarcidin, polystyrene-supported DBU (PDBU) was found to be invaluable to the clean preparation of the highly labile Schmidt donor of L-kedarosamine. By further recognition that the C4-alcohol should be left free for favorable acceptor reactivity, we could for the first time successfully assemble the C13-O-alpha-glycoside of the ansamacrolide substructure of the kedarcidin chromophore.

Keywords:Natural enediynes, Total synthesis studies, Glycosylation
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17123
Deposited On:16 Apr 2015 13:57

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