NEIGHBORING-GROUP PARTICIPATION IN THE CHROMIUM TRIOXIDE OXIDATION OF STEROIDAL 4,5-EPOXIDES - X-RAY MOLECULAR-STRUCTURE OF 4-BETA,6-BETA,17-BETA-TRIACETOXY-3-BETA,5-ALPHA-DIHYDROXYANDROSTANE

被引:4
作者
FLAIH, N [1 ]
HANSON, JR [1 ]
HITCHCOCK, PB [1 ]
机构
[1] UNIV SUSSEX,SCH MOLEC SCI,BRIGHTON BN1 9QJ,E SUSSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 05期
关键词
D O I
10.1039/p19910001085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chromium trioxide oxidation of steroidal 3-beta-acetoxy-4-alpha,5-alpha-epoxides affords products in which the acetoxy group has migrated to the 4-beta-position whilst oxidation of the isomeric 4-beta,5-beta-epoxides affords 5-alpha-hydroxy-4-ketones without rearrangement. The effect of 3-chloro and 6-beta-acetoxy substituents is explored.
引用
收藏
页码:1085 / 1089
页数:5
相关论文
共 10 条
[1]   NEIGHBORING GROUP PARTICIPATION IN CLEAVAGE OF SOME STEROIDAL ACETOXY-EPOXIDES [J].
CAMPION, TH ;
MORRISON, GA ;
WILKINSON, JB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (23) :2508-2516
[2]   STEROIDS AND RELATED COMPOUNDS .6. THE STEREOCHEMICAL CONFIGURATION AND DEHYDRATION OF THE ISOMERIC ANDROSTANE-3-5-6-TRIOL-ONES [J].
DAVIS, M ;
PETROW, V .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (OCT) :2536-2539
[3]   PREPARATION OF STEROIDAL 5-BETA,6-BETA-EPOXIDES AND THEIR OXIDATION BY CHROMIUM TRIOXIDE [J].
HANSON, JR ;
TRUNEH, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :2001-2003
[4]  
HANSON JR, 1988, J CHEM SOC P1, P331
[5]   NEIGHBORING GROUP EFFECTS .1. EFFECT OF ALPHA-HYDROXY-GROUPS AND ALPHA-ACE-TOXY-GROUPS ON THE RING-OPENING OF STEROIDAL 4,5-EPOXIDES [J].
ISHIGURO, M ;
SAITO, H ;
HIRANO, Y ;
IKEKAWA, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (11) :2503-2506
[6]  
JULIA S, 1966, B SOC CHIM FR, P1106
[7]  
JULIA S, 1966, B SOC CHIM FR, P1114
[8]   PHOTOCHEMICAL REACTIONS .41. BIOMOLECULAR PHOTOREDUCTION OF CYCLIC KETONES CYCLIC BETA-HYDROXYKETONES AND CYCLIC ALPHA BETA-EPOXYKETONES [J].
KELLER, P ;
EGGART, G ;
WEHRLI, H ;
SCHAFFNE.K ;
JEGER, O .
HELVETICA CHIMICA ACTA, 1967, 50 (08) :2259-&
[9]  
KNOF L, 1961, LIEBIGS ANN CHEM, V647, P53
[10]   PREPARATION AND ISOMERIZATION OF SOME STEROIDAL HYDROXY EPOXIDES [J].
MORRISON, GA ;
WILKINSON, JB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2003-2007