Synthesis, Structure, and Reactivity of Secosteroids Containing a Medium‐Sized Ring. Part 36.  Transannular photocyclization of some unsaturated 5,10‐secosteroidal ketones: A reevaluation | Zendy

Heckendorn Roland | Zendy; Fuhrer Hermann | Zendy; Kalvoda Jaroslav | Zendy; Lorenc Ljubinka | Zendy; Pavlović Vladimir | Zendy; Mihailović Mihailo Lj. | Zendy

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Synthesis, Structure, and Reactivity of Secosteroids Containing a Medium‐Sized Ring. Part 36. Transannular photocyclization of some unsaturated 5,10‐secosteroidal ketones: A reevaluation

Author(s) -

Heckendorn Roland,

Fuhrer Hermann,

Kalvoda Jaroslav,

Lorenc Ljubinka,

Pavlović Vladimir,

Mihailović Mihailo Lj.

Publication year - 1995

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.19950780519

Subject(s) - oxetane , chemistry , intramolecular force , reactivity (psychology) , ring (chemistry) , stereochemistry , irradiation , transformation (genetics) , medicinal chemistry , organic chemistry , biochemistry , pathology , nuclear physics , gene , medicine , physics , alternative medicine

The structures 9 and 8 are proposed for the single isolated irradiation product of 5‐oxo‐5,10‐secocholest‐1(10)‐en‐3α‐yl acetate ( 6 ) [2] and for the minor product of irradiation of 5‐oxo‐5,10‐secocholest‐1(10)‐en‐3β‐yl acetate ( 1 ) [3], respectively. These compounds are formed in an alternative reaction with respect to the originally observed intramolecular Paterro ‐ Büchi photoprocess (transformation of 1 to oxetane 2 ). The formerly postulated ‘active’ conformations for 1 and 6 still allow explanation of their generation.

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