DIRECT OXYFUNCTIONALIZATION AT UNACTIVATED SITES - SYNTHESIS OF 5-BETA-HYDROXYSTEROIDS BY PERFLUORODIALKYLOXAZIRIDINES

被引：42

作者：

ARNONE, A ^{[1
]}

CAVICCHIOLI, M ^{[1
]}

MONTANARI, V ^{[1
]}

RESNATI, G ^{[1
]}

机构：

[1] CNR,CTR STUDIO SOSTANZE ORGAN NAT,,DIPARTIMENTO CHIM,I-20131 MILAN,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 19期

关键词：

D O I：

10.1021/jo00098a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By treatment with perfluoro-cis-2-n-butyl-3-n-propyloxaziridine 1a, 5 beta-steroids 2a-i (belonging to different classes, such as androstanes, cholestanes, pregnanes, and cholanic acids) have been hydroxylated in good yields and with complete site selectivity and stereoselectivity to corresponding 5 beta-hydroxy derivatives 3a-i independently from the presence of halide, ketone, carboxylic acid, and ester moieties on C-3, C-11, C-12, C-17, C-20, C-21, and C-24.

引用

页码：5511 / 5513

页数：3

共 55 条

[1] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS
ADAM, W
CURCI, R
EDWARDS, JO
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) : 205 - 211
[2] THE SELECTIVE OXIDATION OF PROTECTED CHOLESTANOL DERIVATIVES USING THE GIF SYSTEM
BARTON, DHR
GOKTURK, AK
MORZYCKI, JW
MOTHERWELL, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (03): : 583 - 585
[3] REGIOSELECTIVE AND STEREOSELECTIVE REMOTE HYDROXYLATIONS OF THE A-RING OF STEROIDS - A NOVEL ROUTE TO 5-ALPHA STEROIDS WITH CIS-COUPLED A-RING AND B-RING
BEGUE, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (22) : 4268 - 4271
[4] OXYFUNCTIONALIZATION OF STEROIDS BY DIOXIRANES - SITE AND STEREOSELECTIVE C-14 AND C-17 HYDROXYLATION OF PREGNANE AND ANDROSTANE STEROIDS
BOVICELLI, P
LUPATTELLI, P
FIORINI, V
MINCIONE, E
[J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6103 - 6104
[5] A HIGHLY REGIOSELECTIVE AND STEREOSELECTIVE-C5 OXYFUNCTIONALIZATION OF COPROSTANE STEROIDS BY DIOXIRANES - AN IMPROVED ACCESS TO PROGESTOGEN AND ANDROGEN HORMONES
BOVICELLI, P
GAMBACORTA, A
LUPATTELLI, P
MINCIONE, E
[J]. TETRAHEDRON LETTERS, 1992, 33 (48) : 7411 - 7412
[6] OXIDATION OF NATURAL TARGETS BY DIOXIRANES - OXYFUNCTIONALIZATION OF STEROIDS
BOVICELLI, P
LUPATTELLI, P
MINCIONE, E
PRENCIPE, T
CURCI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) : 2182 - 2184
[7] OXIDATION OF NATURAL TARGETS BY DIOXIRANES .2. DIRECT HYDROXYLATION AT THE SIDE-CHAIN C-25 OF CHOLESTANE DERIVATIVES AND OF VITAMIN-D3 WINDAUS-GRUNDMANN KETONE
BOVICELLI, P
LUPATTELLI, P
MINCIONE, E
PRENCIPE, T
CURCI, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) : 5052 - 5054
[8] CONVERSION OF CHOLESTANOL TO 12-KETOCHOLESTANOL AND TO DELTA14-CHOLESTENOL AND DELTA8(14)-CHOLESTENOL BY REMOTE OXIDATION
BRESLOW, R
BALDWIN, SW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 732 - &
[9] BROWN DS, 1992, J CHEM RES-S, P28
[10] MILD AND SELECTIVE OXYGENATION OF SULFIDES TO SULFOXIDES AND SULFONES BY PERFLUORO-CIS-2,3-DIALKYLOXAZIRIDINES
DESMARTEAU, DD
PETROV, VA
MONTANARI, V
PREGNOLATO, M
RESNATI, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2762 - 2765

← 1 2 3 4 5 6 →