SYNTHESIS OF 17-(2-METHOXY-3-OXAZOLIN-4-YL), 17-(3-OXAZOLIN-4-YL), AND 17-(2-OXAZOLIN-4-YLIDENE)-SUBSTITUTED STEROIDS AND THEIR USE AS PRECURSORS OF CORTICOSTEROIDS

被引：3
|
作者：
VANLEUSEN, D [1 ]
BATIST, JNM [1 ]
LEI, J [1 ]
VANECHTEN, E [1 ]
BROUWER, AC [1 ]
VANLEUSEN, AM [1 ]
机构：
[1] UNIV GRONINGEN,CTR CATALYSIS & SYNTH,DEPT CHEM,9747 AG GRONINGEN,NETHERLANDS
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 19期
关键词：
D O I：
10.1021/jo00098a024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
17-(Isocyanotosylmethylene)steroids 4 are useful intermediates in the conversion of 17-oxosteroids into 17-(hydroxyacetyl)steroids. The 21-CH2OH group is effectively introduced by a base-mediated reaction of compounds 4 with formaldehyde and MeOH to give 17-(2-methoxy-3-oxazolin-4-yl) derivatives 12, which by acid hydrolysis give 17-(hydroxyacetyl)steroids 10 and 16 in high yields. Partial hydrolysis of the same oxazoline derivatives 12 provides the 17-(hydroxyacetyl) cortico side chain of 13 equipped with a formyl-protected hydroxy group. 3-Oxazolinyl and 2-oxazolinylidene steroid derivatives 19, 20, and 21, without a 2-methoxy substituent, are discussed as alternatives of 12.
引用
收藏
页码：5650 / 5657
页数：8
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