OXIDATION OF HOMOALLYLIC STEROID ALCOHOLS WITH PYRIDINIUM CHLOROCHROMATE - THE SYNTHESIS OF STEROIDAL 4-EN-3,6-DIONES

被引：6

作者：

BLASZCZYK, K ^{[1
]}

PARYZEK, Z ^{[1
]}

机构：

[1] ADAM MICKIEWICZ UNIV POZNAN,FAC CHEM,PL-60780 POZNAN,POLAND

来源：

SYNTHETIC COMMUNICATIONS | 1994年 / 24卷 / 22期

关键词：

D O I：

10.1080/00397919408010248

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Prolonged oxidation of steroidal homoallylic Delta(5)-3-alcohols with pyridinium chlorochromate (PCC) in dichloromethane affords the corresponding Delta(4)-3,6-diones via the intermediate Delta(5)-3-one and not a Delta(4)-3-one.

引用

页码：3255 / 3259

页数：5

共 13 条

[1]

BALDWIN O, 1972, J CHEM SOC P1, P1889

[2]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[3]

DAURIA M, 1985, SYNTHESIS-STUTTGART, P988

[4] CHOLESTEROL AND COMPANIONS .2. EXHAUSTIVE DICHROMATE OXIDATION [J].

FIESER, LF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (18) :4386-4394

[5]

GONDOS G, 1990, LIEBIGS ANN CHEM, P213

[6] INTRAMOLECULAR CATALYSIS .2. ELECTROPHILIC ANCHIMERIC ASSISTANCE BY A HYDROXY-GROUP IN OPENING OF STEROIDAL EPOXIDES BY AZIDE ANIONS [J].

HOUMINER, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (17) :1663-1669

[7] FURTHER-STUDIES ON THE SELECTIVE OXIDATION OF STEROIDAL ALLYLIC ALCOHOLS [J].

PARISH, EJ ;

SCOTT, AD ;

DICKERSON, JR ;

DYKES, W .

CHEMISTRY AND PHYSICS OF LIPIDS, 1984, 35 (04) :315-320

[8] A NOVEL SYNTHESIS OF STEROIDAL DELTA-4,3,6-DIONES USING PYRIDINIUM CHLOROCHROMATE (PCC) [J].

PARISH, EJ ;

KIZITO, SA ;

HEIDEPRIEM, RW .

SYNTHETIC COMMUNICATIONS, 1993, 23 (02) :223-230

[9] SELECTIVE OXIDATION OF STEROIDAL HOMOALLYLIC ALCOHOLS USING PYRIDINIUM CHLOROCHROMATE (PPC) [J].

PARISH, EJ ;

LUO, C ;

PARISH, S ;

HEIDEPRIEM, RW .

SYNTHETIC COMMUNICATIONS, 1992, 22 (19) :2839-2847

[10] A SIMPLIFIED, ONE-STEP SYNTHESIS OF CHOLEST-5-EN-3-ONE [J].

PARISH, EJ ;

CHITROKORN, S .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1983, 15 (05) :365-367

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