A total synthesis of OSW-1

被引：41

作者：

Xue, Jie ^{[1
]}

Liu, Peng ^{[1
]}

Pan, Yanbin ^{[1
]}

Guo, Zhongwu ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 01期

关键词：

D O I：

10.1021/jo7018812

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new and practical method was developed to synthesize OSW-1, a natural saponin with potent antitumor activities, from (+)-dehydroisoandrosterone, L-arabinose, and D-xylose on gram scale. The synthesis was achieved in 10 linear steps with an overall yield of 6.4% starting from (+)-dehydroisoandrosterone.

引用

收藏

页码：157 / 161

页数：5

相关论文

共 32 条

[1] A NEW SYNTHESIS OF CHOLESTEROL AND RELATED C27 STEROIDS [J].

CHAUDHURI, NK ;

NICKOLSON, R ;

WILLIAMS, JG ;

GUT, M .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (12) :3767-+

[2] Synthesis of 5(6)-dihydro-OSW-1 by using the intact skeleton of tigogenin [J].

Chen, Li-Jun ;

Xu, Qi-Hai ;

Huang, Hao ;

Lin, Jing-Rong ;

Tian, Wei-Sheng .

TETRAHEDRON LETTERS, 2007, 48 (19) :3475-3477

[3] Synthesis of OSW-1 analogs with modified side chains and their antitumor activities [J].

Deng, LH ;

Wu, H ;

Yu, B ;

Jiang, MR ;

Wu, JR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (11) :2781-2785

[4] First total synthesis of an exceptionally potent antitumor saponin, OSW-1 [J].

Deng, SJ ;

Yu, B ;

Lou, Y ;

Hui, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :202-208

[5] Cephalostatin support studies 12. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1 [J].

Guo, CX ;

Fuchs, PL .

TETRAHEDRON LETTERS, 1998, 39 (10) :1099-1102

[6] On the relationship of OSW-1 to the cephalostatins [J].

Guo, CX ;

LaCour, TG ;

Fuchs, PL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (03) :419-424

[7]

Kruszewska A, 2006, POL J CHEM, V80, P611

[8] ACYLATED CHOLESTANE GLYCOSIDES FROM THE BULBS OF ORNITHOGALUM-SAUNDERSIAE [J].

KUBO, S ;

MIMAKI, Y ;

TERAO, M ;

SASHIDA, Y ;

NIKAIDO, T ;

OHMOTO, T .

PHYTOCHEMISTRY, 1992, 31 (11) :3969-3973

[9] Synthesis of OSW-1 analogues and a dimer and their antitumor activities [J].

Ma, XQ ;

Yu, B ;

Hui, YZ ;

Miao, ZH ;

Ding, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (16) :2153-2156

[10] Synthesis of glycosides bearing the disaccharide of OSW-1 or its 1 → 4-linked analogue and their antitumor activities [J].

Ma, XQ ;

Yu, B ;

Hui, YZ ;

Xiao, D ;

Ding, J .

CARBOHYDRATE RESEARCH, 2000, 329 (03) :495-505

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