TY - JOUR
T1 - Total synthesis of vineomycin B2
AU - Kusumi, Shunichi
AU - Tomono, Satoshi
AU - Okuzawa, Shunsuke
AU - Kaneko, Erika
AU - Ueda, Takashi
AU - Sasaki, Kaname
AU - Takahashi, Daisuke
AU - Toshima, Kazunobu
PY - 2013/10/23
Y1 - 2013/10/23
N2 - 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.
AB - 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.
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U2 - 10.1021/ja407827n
DO - 10.1021/ja407827n
M3 - Article
C2 - 24074200
AN - SCOPUS:84886455893
SN - 0002-7863
VL - 135
SP - 15909
EP - 15912
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 42
ER -