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

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

doi:10.1021/ol036353v

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

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

Authors

Isao Ohashi¹, Martin J Lear, Fumihiko Yoshimura, Masahiro Hirama

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, COE, Sendai 980-8578, Japan.

PMID: 14986958
DOI: 10.1021/ol036353v

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]