Regioselective synthesis of pyrroloquinolines - Approaches to martinelline.

Authors
Hadden, M Stevenson, PJ
Citation
M. Hadden et Pj. Stevenson, Regioselective synthesis of pyrroloquinolines - Approaches to martinelline., TETRAHEDR L, 40(6), 1999, pp. 1215-1218
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
6
Year of publication
1999
Pages
1215 - 1218
Database
ISI
SICI code
0040-4039(19990205)40:6<1215:RSOP-A>2.0.ZU;2-L
Abstract
Indium trichloride catalysed Diels-Alder reaction of imines derived from an ilines with cyclic enamides regioselectively gave the biologically importan t pyrroloquinoline nucleus, with a cis ring junction, in moderate yield. Al though the euo:endo selectivity was in most cases poor, these isomers are r eadily separated by flash chromatography. The functionality tolerated at bo th C2 and C7 should allow further elaboration to Martinelline (C) 1999 Publ ished by Elsevier Science Ltd. All rights reserved.