ESTABLISHMENT OF EFFICIENT HYDROXYLATION AT ANGULAR POSITION OF 4A-ARYL-TRANS-DECAHYDROISOQUINOLINES

Authors
KAWAI K KAWAMURA K NAGASE H
Citation
K. Kawai et al., ESTABLISHMENT OF EFFICIENT HYDROXYLATION AT ANGULAR POSITION OF 4A-ARYL-TRANS-DECAHYDROISOQUINOLINES, Heterocycles, 48(5), 1998, pp. 949-959
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
48
Issue
5
Year of publication
1998
Pages
949 - 959
Database
ISI
SICI code
0385-5414(1998)48:5<949:EOEHAA>2.0.ZU;2-X
Abstract
Efficient hydroxylation method at angular 8a position of 4a-aryl-trans -decahydroisoquinolines was described. By utilizing the transformation process, syntheses of 2-methyl- and -methoxyphenyl)-6-oxo-trans-decah ydroisoquinolines (13 and 17), the useful molecules as an opioid messa ge substructure, were attained. The key step in this transformation wa s N-protection of enamine intermediate by 2, 2,2-trichloroethoxycarbon yl chloride and subsequent epoxidation and hydride reduction.