18-羟基脱氧皮质酮的合成改进
Improved synthesis of 18-hydroxydeoxycorticosterone.
作者信息
Slaunwhite W D, Solo A J
出版信息
J Pharm Sci. 1975 Jan;64(1):168-9. doi: 10.1002/jps.2600640142.
PMID:1133696
Abstract
Hypoiodite photolysis of 3beta-acetoxy-5-pragnen-20beta-olgave 3beta-acetoxy-5-pregnene-18,20-lactone in 46% yield. Lithium aluminum hydride reduction of the latter afforded 3beta, 18,20beta-trihydroxy-5-pregnen (91% yield) which, on Oppenauer oxidation, was converted to 18-hydroxyprogesterone (66%). Lead tetraacetate oxidation followed by mild saponification gave 18-hydroxydeoxycorticosterone (58%) yield).
摘要
3β - 乙酰氧基 - 5 - 孕烯 - 20β - 醇经次碘酸盐光解得到产率为46%的3β - 乙酰氧基 - 5 - 孕烯 - 18,20 - 内酯。后者经氢化铝锂还原得到产率为91%的3β,18,20β - 三羟基 - 5 - 孕烯，该产物经欧芬脑尔氧化转化为18 - 羟孕酮（产率66%）。经四乙酸铅氧化后再进行温和皂化得到18 - 羟基脱氧皮质酮（产率58%）。
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