Total synthesis of vineomycin B2.


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.

DOI: 10.1021/ja407827n

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@article{Kusumi2013TotalSO, title={Total synthesis of vineomycin B2.}, author={Shunichi Kusumi and Satoshi Tomono and Shunsuke Okuzawa and Erika Kaneko and Takashi Ueda and Kaname Sasaki and Daisuke Takahashi and Kazunobu Toshima}, journal={Journal of the American Chemical Society}, year={2013}, volume={135 42}, pages={15909-12} }