CYCLIZATIONS OF TRYPTOPHANS .5. TRIFLUOROACETYLATION OF N-B-METHOXYCARBONYL-L-TRYPTOPHAN METHYL-ESTER IN PYRIDINE

Authors
ANTHONI U CHRISTOPHERSEN C NIELSEN PH PEDERSEN EJ
Citation
U. Anthoni et al., CYCLIZATIONS OF TRYPTOPHANS .5. TRIFLUOROACETYLATION OF N-B-METHOXYCARBONYL-L-TRYPTOPHAN METHYL-ESTER IN PYRIDINE, Acta chemica Scandinavica, 51(3), 1997, pp. 407-410
Citations number
8
Categorie Soggetti
Chemistry,Biology
Journal title
Acta chemica Scandinavica → ACNP
ISSN journal
0904213X
Volume
51
Issue
3
Year of publication
1997
Supplement
S
Pages
407 - 410
Database
ISI
SICI code
0904-213X(1997)51:3<407:COT.TO>2.0.ZU;2-B
Abstract
N-b-Methoxycarbonyl-L-tryptophan methyl ester (1) reacts with trifluor oacetic anhydride in pyridine to give aS)-3a-(N-trifluoroacetyl-1,4-di hydro-4-pyridyl)-1 ethoxycarbonyl-2-methoxycarbonyl-8-trifluoroacetyl -1,2,3,3a,8,8a-hexahydropyrrolo [2,3-b]indole (4). In addition -triflu oroacetyl-N-b-methoxy-carbonyl-L-tryptophan methyl ester (1b) and two diastereomeric dro-2-trifluoroacetoxy-1',5'-bis(methoxycarbonyl)- 2'-h ydroxy-2'-trifluoro-methylspiro [indole-3,3'-pyrrolidine] (5a/5b) are formed.