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D-Ring modification of steroids: synthesis of isoxazole annulated steroids from des D-formyl alkyne via 1,3-dipolar cycloaddition reaction
Synthetic Communications ( IF 1.8 ) Pub Date : 2021-07-26 , DOI: 10.1080/00397911.2021.1955930
Geetmani Singh Nongthombam 1 , Romesh Chandra Boruah 1
Affiliation  

Abstract

The reaction of 17,17-dichloro-androst-16(E)-chloromethylene with secondary amine base afforded substitution products of exocyclic D-ring ketones, in contrast to the reaction of alkaline base which cleaved steroidal D-ring to des-D formyl alkyne. The des-D formyl alkyne was employed to prepare D-ring annulated isoxazolo steroid via 1,3-dipolar nitrile oxide cycloaddition reaction.



中文翻译:

类固醇的 D 环修饰:通过 1,3-偶极环加成反应从脱 D-甲酰基炔合成异恶唑环状类固醇

摘要

17,17-二氯-雄甾醇-16( E )-氯亚甲基与仲胺碱的反应提供环外D-环酮的取代产物,而碱性碱的反应将甾体D-环裂解为脱-D-甲酰基炔烃。脱-D 甲酰基炔用于通过 1,3-偶极腈氧化物环加成反应制备 D 环环化异恶唑类固醇。

更新日期:2021-08-25
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