Novel zinc mediated indole ring opening of isoreserpine

Authors
Berner, M Tolvanen, A Lounasmaa, M Jokela, R
Citation
M. Berner et al., Novel zinc mediated indole ring opening of isoreserpine, HETEROCYCLE, 51(12), 1999, pp. 2941-2948
Citations number
12
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
12
Year of publication
1999
Pages
2941 - 2948
Database
ISI
SICI code
0385-5414(199912)51:12<2941:NZMIRO>2.0.ZU;2-O
Abstract
Reaction of reserpine'(1) with Zn/TFA resulted in isoreserpine (2), dihydro compound (7), and amino compound (8) via initial epimerization at C-3. The latter two compounds constitute a novelty in indole alkaloid chemistry: th e dihydro compound (7) possesses unusual H-2/H-7 cis and H-2/H-3 trans rela tionships, whereas the amino compound (8) displays a novel zinc mediated in dole ring scission.