Total Synthesis of Vineomycin B2

被引：26

作者：

Kusumi, Shunichi ^{[1
]}

Tomono, Satoshi ^{[1
]}

Okuzawa, Shunsuke ^{[1
]}

Kaneko, Erika ^{[1
]}

Ueda, Takashi ^{[1
]}

Sasaki, Kaname ^{[1
]}

Takahashi, Daisuke ^{[1
]}

Toshima, Kazunobu ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 42期

关键词：

C-ARYLGLYCOSYLATION; METHYL-ESTER; GLYCOSYLATION; ARYL; LACTONAMYCIN; GLYCOSIDES; STRATEGY;

D O I：

10.1021/ja407827n

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of vineomycin B-2 (1) has been accomplished. The aglycon segment, a vineomycinone B-2 derivative, and the glycon segment, an alpha-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.

引用

页码：15909 / 15912

页数：4

共 50 条

[1] Total synthesis of vineomycin B2
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
Toshima, K. (toshima@applc.keio.ac.jp), 1600, American Chemical Society (135):
[2] TOTAL SYNTHESIS OF VINEOMYCIN-B2 AGLYCON
DANISHEFSKY, SJ
BIING, JU
QUALLICH, G
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (08) : 2453 - 2455
[3] Toward the total synthesis of vineomycin B2:: application of an efficient glycosylation methodology using 2,3-unsaturated sugars
Sasaki, Kaname
Matsumura, Shuichi
Toshima, Kazunobu
TETRAHEDRON LETTERS, 2007, 48 (39) : 6982 - 6986
[4] Total synthesis of topsentolide B2
Fernandes, Rodney A.
Kattanguru, Pullaiah
TETRAHEDRON LETTERS, 2011, 52 (15) : 1788 - 1790
[5] TOTAL SYNTHESIS OF THROMBOXANE B2
NELSON, NA
JACKSON, RW
TETRAHEDRON LETTERS, 1976, (37) : 3275 - 3278
[6] Total synthesis of (+)-allocyathin B2
Trost, BM
Dong, L
Schroeder, GM
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) : 2844 - 2845
[7] Total synthesis of cryptopyranmoscatone B2
Hu, Chao
Zhao, Ziyang
Nie, Pengpeng
Du, Yuguo
Feng, Fu
Liu, Jun
TETRAHEDRON, 2022, 105
[8] DIRECT TOTAL SYNTHESIS OF THROMBOXANE B2 (+)
COREY, EJ
SHIBASAKI, M
KNOLLE, J
SUGAHARA, T
TETRAHEDRON LETTERS, 1977, (09) : 785 - 788
[9] STEREOSPECIFIC, TOTAL SYNTHESIS OF THROMBOXANE B2
HANESSIAN, S
LAVALLEE, P
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (03): : 562 - 565
[10] Enantioselective total synthesis of (-)-cyathin B2
Kobayakawa, Yu
Nakada, Masahisa
JOURNAL OF ANTIBIOTICS, 2014, 67 (06): : 483 - 485

← 1 2 3 4 5 →