DIASTEREOSELECTIVE SYNTHESIS OF AN ISOPROSTANE - (+ -)-8-EPI-PGF(2-ALPHA) ETHYL-ESTER/

Authors
TABER DF HERR RJ GLEAVE DM
Citation
Df. Taber et al., DIASTEREOSELECTIVE SYNTHESIS OF AN ISOPROSTANE - (+ -)-8-EPI-PGF(2-ALPHA) ETHYL-ESTER/, Journal of organic chemistry, 62(1), 1997, pp. 194-198
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
1
Year of publication
1997
Pages
194 - 198
Database
ISI
SICI code
0022-3263(1997)62:1<194:DSOAI->2.0.ZU;2-7
Abstract
A total synthesis of the isoprostane (+/-)-8-epi-PGF(2a) ethyl eater ( 5) is described, based on the diastereoselective cyclization of alpha- diazo ketone 7. This ketone is assembled by aldol condensation between a-diazo ketone 8 and aldehyde 9. The sequential alpha-diazo ketone al dol/insertion described here offers a powerful new approach to cycloal kane construction.