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.
Department of Applied Chemistry, Faculty of Science and Technology, Keio University , 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Shunichi
S
Kusumi
Satoshi
S
Tomono
Shunsuke
S
Okuzawa
Erika
E
Kaneko
Takashi
T
Ueda
Kaname
K
Sasaki
Daisuke
D
Takahashi
Kazunobu
K
Toshima
D000880:Anthraquinones / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure
D000880:Anthraquinones; C024277:vineomycin B2