PARTICIPATION OF THE 19-SUBSTITUENT IN THE CONVERSION OF 19-HYDROXYANDROST-4-ENE-3,17-DIONE INTO THE CORRESPONDING 4,5-DIOSPHENOL

被引：6

作者：

HRYCKO, S ^{[1
]}

MORAND, P ^{[1
]}

机构：

[1] UNIV OTTAWA,OTTAWA CARLETON CHEM INST,DEPT CHEM,OTTAWA K1N 6N5,ONTARIO,CANADA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 11期

关键词：

D O I：

10.1039/p19900002899

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 4,19-dihydroxyandrost-4-ene-3,17-dione from 19-hydroxy-4β,5-epoxy-5βandrostane-3,17-dione and from 4β,5,19-trihydroxy-5β-androstane-3,17-dione is described. Under various reaction conditions other products are obtained as a result of participation of the 19hydroxy group to form cyclic ethers. The formation of two of these products, 4α,5-isopropylidene3α-hydroxy-3β,19-epoxy- 5α-androstan-17-one and 4α-hydroxy-4β,19-epoxy-5α- androstane-3,17dione, can be avoided by treatment of the aforementioned trihydroxy dione with acetic acid in the presence of HCI.

引用

页码：2899 / 2904

页数：6

共 24 条

[21]

MORISAWA Y, 1969, CHEM PHARM BULL, V17, P1206

[22] REGIOSPECIFIC SYNTHESES OF MODIFIED STEROID-HORMONES .6. ALPHA-MODE, ALPHA'-MODE, AND BETA-MODE REACTIONS OF HYDROGEN HALIDES WITH 1,2-EPOXY-3-OXO-ANDROSTANES AND 4,5-EPOXY-3-OXO-ANDROSTANES AND 4,5-EPOXY-3-OXO-ANDROESTRANES [J].

NEEMAN, M ;

OGRODNIC.JS .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (16) :2941-2949

[23]

RAO PN, 1961, J CHEM SOC, P4769

[24]

SILVERSTEIN RM, 1981, SPECTROMETRIC IDENTI, P316

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