Synthesis of 5(6)-dihydro-OSW-1 by using the intact skeleton of tigogenin

被引：26

作者：

Chen, Li-Jun

Xu, Qi-Hai

Huang, Hao

Lin, Jing-Rong

Tian, Wei-Sheng

机构：

[1] Shanghai Normal Univ, Lab Resource Chem, Shanghai 200234, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 19期

关键词：

D O I：

10.1016/j.tetlet.2007.03.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

5(6)-Dihydro-OSW-1 (1), an analogue of OSW-1 with the potent anticancer activity, was synthesized by utilizing the intact skeleton of tigogenin in 13 steps in 9.0% overall yield. This synthesis demonstrated an effective and reasonable synthetic strategy for bioactive steroids with side chains as compared with their routine synthesis. (c) 2007 Elsevier Ltd. All rights reserved.

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收藏

页码：3475 / 3477

页数：3

相关论文

共 19 条

[1]

ARTHUR FK, 1985, J ORG CHEM, V50, P2359

[2]

Deng LH, 2004, CHINESE J CHEM, V22, P994

[3]

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

[4]

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

[5]

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

[6]

Sterols. CXIII. Sapogenins. XLII. The conversion of the sapogenins to the pregnenolones [J].

Marker, RE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :3350-3352

[7]

Cholestane glycosides with potent cytostatic activities on various tumor cells from Ornithogalum saundersiae bulbs [J].

Mimaki, Y ;

Kuroda, M ;

Kameyama, A ;

Sashida, Y ;

Hirano, T ;

Oka, K ;

Maekawa, R ;

Wada, T ;

Sugita, K ;

Beutler, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (05) :633-636

[8]

Some reactions of 16α,17α-oxido-steroids:: a study related to the synthesis of the potent anti-tumor Saponin OSW-1 aglycone [J].

Morzycki, JW ;

Gryszkiewicz, A ;

Jastrzebska, I .

TETRAHEDRON LETTERS, 2000, 41 (19) :3751-3754

[9]

A highly efficient synthesis of 22-deoxy-OSW-1 by utilizing the intact skeleton of diosgenin [J].

Qin, HJ ;

Tian, WS ;

Lin, CW .

TETRAHEDRON LETTERS, 2006, 47 (19) :3217-3219

[10]

STEROIDS .81. TRANSFORMATION OF SAPOGENINS TO ANDROGENS AND ESTROGENS - BECKMANN REARRANGEMENT OF DELTA-16-20-KETOSTEROIDS [J].

ROSENKRANZ, G ;

MANCERA, O ;

SONDHEIMER, F ;

DJERASSI, C .

JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (05) :520-522