ASYMMETRIC-SYNTHESIS OF PROTOBERBERINE ALKALOIDS VIA A TANDEM NUCLEOPHILIC-ADDITION AND INTRAMOLECULAR CYCLIZATION OF A CHIRAL O-TOLUAMIDE ANION WITH 3,4-DIHYDROISOQUINOLINE

Authors
WARRENER RN LIU LG RUSSELL RA
Citation
Rn. Warrener et al., ASYMMETRIC-SYNTHESIS OF PROTOBERBERINE ALKALOIDS VIA A TANDEM NUCLEOPHILIC-ADDITION AND INTRAMOLECULAR CYCLIZATION OF A CHIRAL O-TOLUAMIDE ANION WITH 3,4-DIHYDROISOQUINOLINE, Chemical communications, (22), 1997, pp. 2173-2174
Citations number
22
Categorie Soggetti
Chemistry
Journal title
Chemical communications → ACNP
ISSN journal
13597345
Issue
22
Year of publication
1997
Pages
2173 - 2174
Database
ISI
SICI code
1359-7345(1997):22<2173:AOPAVA>2.0.ZU;2-I
Abstract
The reaction of o-toluamide anions, derived from the (S)-(-)- and (R)- (+)-1-phenylethylamine, with 6, 7-dimethoxy-3, 4-dihydroisoquinoline g ives (13aS)-(-)- and (13aR)-(+)-8-oxoprotoberberine, respectively, wit h enantiomeric excesses > 96%.