SYNTHESIS, STRUCTURE, AND REACTIVITY OF SECOSTEROIDS CONTAINING A MEDIUM-SIZED RING .36. TRANSANNULAR PHOTOCYCLIZATION OF SOME UNSATURATED 5,10-SECOSTEROIDAL KETONES - A REEVALUATION

Authors
HECKENDORN R FUHRER H KALVODA J LORENC L PAVLOVIC V MIHAILOVIC ML
Citation
R. Heckendorn et al., SYNTHESIS, STRUCTURE, AND REACTIVITY OF SECOSTEROIDS CONTAINING A MEDIUM-SIZED RING .36. TRANSANNULAR PHOTOCYCLIZATION OF SOME UNSATURATED 5,10-SECOSTEROIDAL KETONES - A REEVALUATION, Helvetica Chimica Acta, 78(5), 1995, pp. 1291-1297
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
78
Issue
5
Year of publication
1995
Pages
1291 - 1297
Database
ISI
SICI code
0018-019X(1995)78:5<1291:SSAROS>2.0.ZU;2-P
Abstract
The structures 9 and 8 are proposed for the single isolated irradiatio n product of 5-oxo-5,10-secocholest-1(10)-en-3 beta-yl acetate (6) [2] and for the minor product of irradiation of 5-oxo-5,10-secocholest-1( 10)-en-3 gamma-yl acetate (1) [3], respectively. These compounds are f ormed in an alternative reaction with respect to the originally observ ed intramolecular Paterno-Buchi photoprocess (transformation of 1 to o xetane 2). The formerly postulated 'active' conformations for 1 and 6 still allow explanation of their generation.