A synthesis of (+/-)-dihydronitraraine

Authors
Paivia, E Berner, M Tolvanen, A Jokela, R
Citation
E. Paivia et al., A synthesis of (+/-)-dihydronitraraine, HETEROCYCLE, 53(10), 2000, pp. 2241
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
53
Issue
10
Year of publication
2000
Database
ISI
SICI code
0385-5414(20001001)53:10<2241:ASO(>2.0.ZU;2-T
Abstract
A short synthesis of (+/-)-dihydronitraraine (1) from an unknown 5,6,7,g-te trahydroisoquinoline ester (3) is presented. The Fry reaction of tetrahydro isoquinolinium salt (4), followed by cyclization and hydrogenation, gave an alloyohimbane derivative (6), which was reduced to yield dihydronitraraine (1). Complete H-1 NMR and C-13 NMR data of dihydronitraraine (1) and inter mediate (6) are reported.