SOME REACTIONS OF 16-ALPHA,17-ALPHA-OXIDO-5-ALPHA-CHOLESTANE DERIVATIVES, SYNTHESIS OF 17-ALPHA-HYDROXYCHOLEST-4-EN-3-ONE

被引：6

作者：

VELGOVA, H ^{[1
]}

KASAL, A ^{[1
]}

BUDESINSKY, M ^{[1
]}

机构：

[1] ACAD SCI CZECH REPUBL, INST ORGAN CHEM & BIOCHEM, CR-16610 PRAGUE 6, CZECH REPUBLIC

来源：

STEROIDS | 1994年 / 59卷 / 05期

关键词：

EPITESTOSTERONE ANALOG; EPOXIDATION WITH REARRANGEMENT; WAGNER-MEERWEIN REARRANGEMENT; INTRAMOLECULAR HYDROGEN BOND;

D O I：

10.1016/0039-128X(94)90123-6

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Careful epoxidation of the Delta(16)-olefins 3 and 4 yielded 16 alpha,17 alpha-epoxides 5 and 6 which were reduced by lithium aluminium hydride, oxidized, and dehydrated to 17 alpha-hhydroxycholest-4-en-3-one 20, i.e., an epitestosterone homolog containing a well tolerated alkyl group at position 17. Under catalysis of acids, epoxide 5 was rearranged to Delta(13)-16 alpha-alcohol 10. Less careful epoxidation of Delta(16)-olefin 4 with excess of peroxy acid led to products of double epoxidation (Le., epoxidation, rearrangement, and another oxidation) 7 and 12. Structures of products of rearrangement were studied mainly by NMR spectroscopy.

引用

页码：335 / 340

页数：6

共 12 条

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