APPLICATION OF THE MITSUNOBU REACTION IN THE MORPHINE SERIES - PREPARATION OF 6-BETA-AMINO-14-BETA-HYDROXYMORPHINE AND 14-HYDROXYCODEINE DERIVATIVES

Authors
SIMON C HOSZTAFI S MAKLEIT S
Citation
C. Simon et al., APPLICATION OF THE MITSUNOBU REACTION IN THE MORPHINE SERIES - PREPARATION OF 6-BETA-AMINO-14-BETA-HYDROXYMORPHINE AND 14-HYDROXYCODEINE DERIVATIVES, Heterocycles, 38(6), 1994, pp. 1347-1354
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
6
Year of publication
1994
Pages
1347 - 1354
Database
ISI
SICI code
0385-5414(1994)38:6<1347:AOTMRI>2.0.ZU;2-0
Abstract
By the application of the Mitsunobu reaction several 6beta-phthalimido -14beta-hydroxymorphine and 14beta-hydroxycodeine derivatives have bee n synthesized. Cleavage of the phthalimido derivatives with hydrazine hydrate afforded 6beta-amino-14beta-hydroxymorphine and 14beta-hydroxy codeine derivatives. Catalytic hydrogenation of the DELTA7,8 double bo nd offered a stereoselective way for the synthesis of the correspondin g 6beta-amino-14beta-hydroxydihydrocodeine and 14beta-hydroxydihydromo rphine derivatives.