ON THE SYNTHESIS OF THE 7R-OXIRANES OF 5E - AND 5Z-10-OXO-19-NORCHOLECALCIFEROL

Authors
Citation
W. Reischl, ON THE SYNTHESIS OF THE 7R-OXIRANES OF 5E - AND 5Z-10-OXO-19-NORCHOLECALCIFEROL, Monatshefte fuer Chemie, 125(1), 1994, pp. 85-93
Citations number
30
Categorie Soggetti
Chemistry
Journal title
ISSN journal
00269247
Volume
125
Issue
1
Year of publication
1994
Pages
85 - 93
Database
ISI
SICI code
0026-9247(1994)125:1<85:OTSOT7>2.0.ZU;2-1
Abstract
The two title compounds 12b and 13b have been prepared by direct oxida tion of the corresponding 10-oxo-19-norcolcalciferol derivatives 3c an d 4c with MCPBA. The generation of 12b and 13b by treatment of the Del ta(7) epoxidized ethylisoxazolin adducts of 5Z- and 5E-cholecalciferol 8a, 86 and 9a, 9b with Mo(CO)(6) failed, since besides the retroaldol cleavage of the heterocycle a deoxygenation of the oxirane with reten tion of configuration to the Delta(7) double bond occurs.