CYCLOADDITION ROUTE TO 14,17-ETHANO-19-NORSTEROIDS AND 14-ALKYL-19-NORSTEROIDS

被引：38

作者：

BULL, JR ^{[1
]}

THOMSON, RI ^{[1
]}

机构：

[1] CSIR,NATL RES LAB,PRETORIA 0001,SOUTH AFRICA

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 02期

关键词：

D O I：

10.1039/p19900000241

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cycloaddition of phenyl vinyl sulphone to 14,16-dien-17-yl acetates derived from estrone proceeds regio- and stereo-selectively to give intermediates for conversion into 14,17α-ethenoestra-1,3,5(10)-triene-3,17β-diol derivatives and related ring D bridged 19-norsteroids. Oxidati7ve cleavage of the 14α,17α-etheno bridge leads to 14α17α-diformyl- 17β-acetates and to 14α-formyl-17-ketones. Aspects of the chemistry of the 14α-formyl compounds are discussed, and methods are described for their conversion into 14α-metnyl-and 14-hydroxymethyl-19-norsteroids.

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页码：241 / 251

页数：11

相关论文

共 23 条

[1]

ATWAL KS, 1982, HETEROCYCLES, V19, P641

[2]

BARTON DHR, 1981, SYNTHESIS-STUTTGART, P743

[3] 14-METHYL STEROIDS .5. STRUCTURAL FEATURES INFLUENCING STEREOSELECTIVITY OF 14-METHYLATION OF 15-OXO-19-NORSTEROIDS - SYNTHESIS OF 14-ALPHA-METHYL-19-NORPROGESTERONE [J].

BISCHOFBERGER, K ;

BULL, JR ;

FLOOR, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (06) :1377-1382

[4] 14-METHYL STEROIDS .3. SYNTHESIS OF (+/-)-14-ALPHA-METHYL-9-BETA-ESTRADIOL AND RELATED 14-ALPHA-METHYL-19-NORSTEROIDS [J].

BISCHOFBERGER, K ;

BULL, JR .

TETRAHEDRON, 1985, 41 (02) :365-374

[5] ANALYSES OF THE 500 MHZ H-1 SPECTRA OF THE 3-METHYL ETHERS OF ESTRONE, ESTRADIOL AND THEIR 14-ALPHA-METHYL ANALOGS [J].

BISCHOFBERGER, K ;

BULL, JR ;

CHALMERS, AA .

MAGNETIC RESONANCE IN CHEMISTRY, 1987, 25 (09) :780-783

[6] 14-METHYL STEROIDS .2. TOTAL SYNTHESIS OF (+/-)-14-ALPHA-METHYL-19-NORSTEROIDS [J].

BULL, JR ;

BISCHOFBERGER, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (11) :2723-2727

[7] CYCLOADDITION ROUTE TO 14-ALPHA-FORMYLESTRONE AND DERIVED 14-ALPHA-SUBSTITUTED PRODUCTS [J].

BULL, JR ;

THOMSON, RI .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (06) :451-453

[8] 14-METHYL STEROIDS .4. SYNTHESIS OF 14-BETA-METHYLESTRADIOL AND RELATED 14-BETA-METHYL-19-NORSTEROIDS [J].

BULL, JR ;

FLOOR, J ;

SEFTON, MA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :37-43

[9] DIENOPHILIC PROPERTIES OF PHENYL VINYL SULFONE AND TRANS-1-(PHENYLSULFONYL)-2-(TRIMETHYLSILYL)ETHYLENE - THEIR UTILIZATION AS SYNTHONS FOR ETHYLENE, 1-ALKENES, ACETYLENE, AND MONOSUBSTITUTED ALKYNES IN THE CONSTRUCTION OF FUNCTIONALIZED 6-MEMBERED RINGS VIA [4 + 2] PI-CYCLOADDITION METHODOLOGY [J].

CARR, RVC ;

WILLIAMS, RV ;

PAQUETTE, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :4976-4986

[10] ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].

CHA, JK ;

CHRIST, WJ ;

KISHI, Y .

TETRAHEDRON, 1984, 40 (12) :2247-2255