PICTET-SPENGLER REACTION OF BIOGENIC-AMINES WITH (2R)-N-GLYOXYLOYLBORNANE-10,2-SULTAM - ENANTIOSELECTIVE SYNTHESIS OF (S)-(-N-METHYLCALYCOTOMINE())

Authors
CZARNOCKI Z MIECZKOWSKI JB KIEGIEL J ARAZNY Z
Citation
Z. Czarnocki et al., PICTET-SPENGLER REACTION OF BIOGENIC-AMINES WITH (2R)-N-GLYOXYLOYLBORNANE-10,2-SULTAM - ENANTIOSELECTIVE SYNTHESIS OF (S)-(-N-METHYLCALYCOTOMINE()), Tetrahedron : asymmetry, 6(12), 1995, pp. 2899-2902
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
12
Year of publication
1995
Pages
2899 - 2902
Database
ISI
SICI code
0957-4166(1995)6:12<2899:PROBW(>2.0.ZU;2-0
Abstract
(2R)-N-Glyoxyloylbornane-10,2-sultam reacted with dopamine hydrochlori de, forming the Pictet-Spengler condensation product, which was furthe r converted into (S)-(+)-N)-methylcalycotomine of high enantiomeric pu rity. The same kind of reaction with tryptamine hydrochloride gave the condensation product with 100% d.e.