A PRACTICAL ASYMMETRIC-SYNTHESIS OF ENT-12-EPI-PGF2-ALPHA METHYL-ESTER

Authors
ROLAND A DURAND T RONDOT B VIDAL JP ROSSI JC
Citation
A. Roland et al., A PRACTICAL ASYMMETRIC-SYNTHESIS OF ENT-12-EPI-PGF2-ALPHA METHYL-ESTER, Bulletin de la Societe chimique de France, 133(11), 1996, pp. 1149-1154
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology,Chemistry
Journal title
Bulletin de la Societe chimique de France → ACNP
ISSN journal
00378968
Volume
133
Issue
11
Year of publication
1996
Pages
1149 - 1154
Database
ISI
SICI code
0037-8968(1996)133:11<1149:APAOEM>2.0.ZU;2-K
Abstract
The chiral cyclopentane formyllactone 1, which is easily obtained from commercially available isopropylidene-D-glucose was converted into en t-12-epi-PGF2 alpha methyl ester 3. The key intermediate was all-cis-f ormyllactone 1 related to ent-Corey lactone 2. The choice of a silyl p rotective group was found to be crucial in avoiding P-elimination obse rved with the benzoyl protective group during oxidation of primary alc ohol and the following Horner-Wadworth-Emmons reaction.