Photochemische Reaktionen. 31. Mitteilung. [1]. Die photochemische Isomerisierung von C(‐10)‐diastereomeren 3‐Oxo‐Δ 1;5 ‐Steroiden | Zendy

Nann B. | Zendy; Wehrli H. | Zendy; Schaffner K. | Zendy; Jeger O. | Zendy

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Photochemische Reaktionen. 31. Mitteilung. [1]. Die photochemische Isomerisierung von C(‐10)‐diastereomeren 3‐Oxo‐Δ 1;5 ‐Steroiden

Author(s) -

Nann B.,

Wehrli H.,

Schaffner K.,

Jeger O.

Publication year - 1965

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19650480729

Subject(s) - chemistry , diastereomer , photodissociation , stereochemistry , medicinal chemistry , photochemistry

The photochemical transformation of 3‐oxo‐17β‐acetoxy‐Δ 1;5 ‐androstadiene ( 2 ) and its 10α‐diastereoisomer 7 has been investigated. With low conversion of 2 , an isomer was produced for which structure 8 (6β‐H) is proposed. After longer photolysis times, both compounds, 2 and 8 , were consumed, and the four stereoisomeric photoproducts 9–12 were obtained. Products 9 and 10 on one hand, and 11 and 12 on the other, are photochemically interconvertible. Dienone 7 yielded a very similar product mixture from which ketones 10 and 12 could be isolated. Further, the presence of a dienone isomer was demonstrated to which structure 8 (6α‐H) is assigned.

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