Regioselective protection of 11-hydroxy group and inversion of configuration at C-15 in m-phenylene PGI(2) derivatives

Authors
Wakita, H Hosono, Y Nagase, H
Citation
H. Wakita et al., Regioselective protection of 11-hydroxy group and inversion of configuration at C-15 in m-phenylene PGI(2) derivatives, HETEROCYCLE, 48(12), 1998, pp. 2559-2571
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
48
Issue
12
Year of publication
1998
Pages
2559 - 2571
Database
ISI
SICI code
0385-5414(199812)48:12<2559:RPO1GA>2.0.ZU;2-X
Abstract
The 15 beta-hydroxy isomer of a m-phenylene PGI(2) derivative was converted to its 15 alpha-hydroxy isomer by regioselective protection of 11-hydroxyl group by acylation using 3,5-dinitrobenzoyl chloride followed by inversion of configuration at C-15. A possibility of the presence of pi-pi interacti on between the benzene ring (electron donor) in m-phenylene PGI(2) derivati ve and that (electron acceptor) in the acid chloride is discussed.