Unusual Ozonolysis of Cholesteryl and Androst-5-en-3beta-yl Acetates in the Presence of Primary Amines. Formation of A-nor-3(5--6alfa)abeo-6beta(H)-5-oxo-steroids, Confirmed by X-ray Analysis

• Autorzy: Paryzek Z. , Koenig H. , Skiera I. , Rychlewska U.
• Języki publikacji: EN

Abstrakty

EN

The reaction of cholesteryl acetate with ozone in the presence of amines has been studied. Besides the expected cleavage products, B-seco-ketoaldehyde and its aldol condensation product, 5-hydroxy-6-formyl-B-nor-5_-cholestane derivative, the abnormal product, 3_-acetoxy-A-nor-3(5_6_)abeo-6_(H)-cholestan-5-one is formed as a result of a new, anomalous cleavage of the primary ozonide. The reaction conditions and isolation procedure were optimized for achieving good yield of the abeo-compound. The X-ray crystal structure analysis confirmed the formation of the unusual steroidal skeleton. It appears to be the first crystallographic analysis of the transformed steroid with A-nor-3(5_6_)abeo skeleton. No product resulting from the amine nucleophilic participation in the cleavage of ozonides was observed.

Słowa kluczowe

EN

anomalous ozonolysis; steroids; X-ray analysis

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 7
• Strony: 921--930
• Opis fizyczny: Bibliogr. 28 poz., rys.

Twórcy

autor

Paryzek Z.

• Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Koenig H.

• Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Skiera I.

• Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Rychlewska U.

• Faculty of Chemistry, A. Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

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