On Steroids part CDVIII -: Allopregnanolone derivatives:: Synthesis of 3α-hydroxy-7α-homo-5α-pregnan-20-one

被引：3
|
作者：
Chodounská, H [1 ]
Kasal, A [1 ]
机构：
[1] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic
来源：
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 2000年 / 65卷 / 07期
关键词：
steroids; epalons; allopregnanolone; GABA(A)-modulators; 3; alpha; 5; alpha-tetrahydroprogesterone; Huang Minlon reduction;
D O I：
10.1135/cccc20001156
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
3 alpha-Hydroxy-7 alpha-homo-5 alpha-pregnan-20-one and 3 alpha-hydroxy-7a-homo-5 alpha-pregnane-7,20-dione were prepared from (20R)-3 alpha-(methoxymethoxy)-7-oxo-5 alpha-pregnan-20-yl benzoate. Homologation of the B ring was carried out by the Demyanov rearrangement of the corresponding cyanohydrin. Alkaline hydrolysis of the protecting group and oxidation of the formed 20-hydroxy group and deprotection of the 3-hydroxy group were performed either with (20R)-3 alpha-(methoxymethoxy)-7-oxo-7a-homo-5 alpha-pregnan-20-ol derivative or with the product of the Huang Minlon deoxygenation at carbon 7.
引用
收藏
页码：1156 / 1162
页数：7
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