SYNTHESIS OF ALPHA,BETA-DEHYDROTRYPTOPHAN BY REACTION OF INDOLE WITH THE BETA-(N-METHYLAMINO)DEHYDROALANINE DERIVATIVE

Authors
NAKAZAWA T ISHII M MUSIOL HJ MORODER L
Citation
T. Nakazawa et al., SYNTHESIS OF ALPHA,BETA-DEHYDROTRYPTOPHAN BY REACTION OF INDOLE WITH THE BETA-(N-METHYLAMINO)DEHYDROALANINE DERIVATIVE, Tetrahedron letters, 39(11), 1998, pp. 1381-1384
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
11
Year of publication
1998
Pages
1381 - 1384
Database
ISI
SICI code
0040-4039(1998)39:11<1381:SOABRO>2.0.ZU;2-6
Abstract
alpha,beta-Dehydrotryptophan 4 is synthesized by a sequence of reactio ns starting with the corresponding serine derivative 1. This procedure includes substitution reaction between indole and the methylamino gro up of the beta-(N-methylamino)dehydroalanine derivative 3 in acetic ac id. The key intermediate 3 is obtained by oxidation of 1 with dimethyl sulfoxide activated by p-toluenesulfonyl chloride, followed by reactio n of the resulting beta-O-tosyldehydroserine 2 with methylamine. (C) 1 998 Elsevier Science Ltd. All rights reserved.