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

被引：33

作者：

Morzycki, JW ^{[1
]}

Gryszkiewicz, A ^{[1
]}

Jastrzebska, I ^{[1
]}

机构：

[1] Univ Bialystok, Inst Chem, PL-15443 Bialystok, Poland

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 19期

关键词：

steroids; sapogenins; lithium compounds; epoxides;

D O I：

10.1016/S0040-4039(00)00484-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Five 16 alpha,17 alpha-oxido-steroids were subjected to acids, bases and lithium hydroperoxide. Acids caused Wagner-Meerwein-type rearrangement irrespective of the side-chain structure. The 16 alpha,17 alpha-epoxides proved resistant to bases unless a C(22)=O group was present; in the case of 22-esters or 22-ketones the oxirane rings were cleaved with base and the corresponding allylic alcohols were formed. The reactions of 16 alpha,17 alpha-oxido-22-carbonyl compounds with lithium hydroperoxide resulted in the epoxide cleavage to the desired 16 beta,17 alpha-diols which underwent further transformations. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3751 / 3754

页数：4

共 6 条

[1] 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

[2] 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

[3] 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

[4] 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

[5] 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

[6] SOME REACTIONS OF 16-ALPHA,17-ALPHA-OXIDO-5-ALPHA-CHOLESTANE DERIVATIVES, SYNTHESIS OF 17-ALPHA-HYDROXYCHOLEST-4-EN-3-ONE [J].

VELGOVA, H ;

KASAL, A ;

BUDESINSKY, M .

STEROIDS, 1994, 59 (05) :335-340

← 1 →