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Synthese und Reaktivität von Estra‐1,3,5,(10)‐trienen mit heterocyclischen Vierringen in 14,15‐Stellung

 

作者: Kurt Ponsold,   Richard Prousa,  

 

期刊: Journal für Praktische Chemie  (WILEY Available online 1986)
卷期: Volume 328, issue 5‐6  

页码: 673-681

 

ISSN:0021-8383

 

年代: 1986

 

DOI:10.1002/prac.19863280503

 

出版商: WILEY‐VCH Verlag GmbH

 

数据来源: WILEY

 

摘要:

Synthesis and Reactivity of Estra‐1,3‐5(10)‐trienes with Heterocyclic Four‐Membered Rings in 14,15‐Position3‐Methoxy‐estra‐1,3,5(10),14‐tetraen‐17β‐ol acetate1and ‐17α‐ol acetate2react with chlorosulfonyl isocyanate in stereospecific manner and good yields to 3‐methoxy‐14β,15β‐[3′,4′‐(N‐chlorosulfonyl‐2′‐oxo‐azetidin)]‐estra‐1,3,5(10)‐trien‐17β‐ol acetate3and ‐17α‐ol acetate4, respectively. Hydrolysis of3and4in the presence of reducing agents affords the N‐unsubstituted oxo‐azetidines5and6, reduction of which gives the azetidines9and10. Cleavage of the azetidine ring yields the amino acid derivatives11and15, from which the oxooxetanes12and13and the hyd

 

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