MECHANISM OF THE HYDROGEN-CHLORIDE CATALYZED ISOMERIZATION OF 5-ALPHA-CHOLEST-8(14)-EN-3-BETA-OL TO 5-ALPHA, 17-BETA-CHOLEST-14-EN-3-BETA-OL - FATE OF THE 17-ALPHA-HYDROGEN ATOM

被引：10

作者：

ABERHART, DJ ^{[1
]}

CHAU, TY ^{[1
]}

CASPI, E ^{[1
]}

机构：

[1] WORCESTER FDN EXPTL BIOL,SHREWSBURY,MA 01545

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 01期

关键词：

D O I：

10.1039/p19790000220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(4R)-[3H,2-14C]Mevalonic acid was incubated with a rat liver homogenate, in the presence of the inhibitor AY-9944, to yield [ 3H3,14C5]cholesta-5,7-dien-3β- ol, which was reduced (Li-NH3) to [17α,20,24R- 3H3,14C5]-5α-cholest-7-en- 3β-ol. [3H3,14C5]-5α- Cholest-7-en-3β-ol was isomerized (platinum-acetic acid-hydrogen) and the resulting [3H3,14C5]-5α- cholest-8(14)-en-3β-ol was acetylated. The acetate was treated with hydrogen chloride in chloroform at -78° followed by aqueous NaHCO 3 to give [20,24R-3H2,14C 5]-5α,17β-cholest-14-en-3β-yl acetate. The isomerization proceeded with the loss of ca. 0.9 atom of tritium. The mechanism of the hydrogen chloride catalysed isomerization is discussed.

引用

页码：220 / 224

页数：5

共 15 条

[1]

ABERHART DJ, 1971, J BIOL CHEM, V246, P1387

[2] READY SYNTHESIS OF 17-ALPHA STEROIDS [J].