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J Am Chem Soc. 2013 Oct 23;135(42):15909-12. doi: 10.1021/ja407827n. Epub 2013 Oct 11.

Total synthesis of vineomycin B2.

Author information

1
Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.

Abstract

The first total synthesis of vineomycin B2 (1) has been accomplished. The aglycon segment, a vineomycinone B2 derivative, and the glycon segment, an α-L-acurosyl-L-rhodinose derivative, were prepared via C-glycosylation using an unprotected sugar and powerful chemoselective O-glycosylation using a 2,3-unsaturated sugar, respectively, as the key steps. Furthermore, effective and simultaneous introduction of the two glycon moieties to the aglycon part by concentration-controlled glycosylation led to the total synthesis of 1.

PMID:
24074200
DOI:
10.1021/ja407827n
[Indexed for MEDLINE]

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