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Synthesis, structure, and reactivity of secosteroids containing a medium‐sized ring. Part 32 . Conformations and photochemical reactivity of some unsaturated 5,10‐secosteroidal ketones
Author(s) -
Lorenc Ljubinka,
Pavlović Vladimir,
Mihailović Mihailo Lj.,
Kalvoda Jaroslav,
Fuhrer Hermann
Publication year - 1991
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.19910740709
Subject(s) - chemistry , intramolecular force , reactivity (psychology) , ring (chemistry) , ketone , stereochemistry , photochemistry , intramolecular reaction , ground state , medicinal chemistry , organic chemistry , medicine , physics , alternative medicine , pathology , quantum mechanics
UV irradiation of the unsaturated ( E )‐5,10‐secosteroidal ketones 1 and 6 results, in addition to ( E / Z )‐isomeri‐zation, in an intramolecular Pateino‐Büchi reaction and, in the case of 1 , in transannular cyclization (along with AcOH elimination). The stereochemistry of the observed intramolecular photoprocesses can be explained in terms of ground‐state conformations of the ( E )‐seco‐ketones 1 and 6 in solution.