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

作者信息

Ohashi Isao, Lear Martin J, Yoshimura Fumihiko, Hirama Masahiro

机构信息

Department of Chemistry, Graduate School of Science, Tohoku University, COE, Sendai 980-8578, Japan.

出版信息

Org Lett. 2004 Mar 4;6(5):719-22. doi: 10.1021/ol036353v.

DOI:10.1021/ol036353v
PMID:14986958
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. [reaction: see text]

摘要

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Org Lett. 2007 May 10;9(10):1923-5. doi: 10.1021/ol070450x. Epub 2007 Apr 18.