SYNTHETIC STUDIES TOWARD DIAZONAMIDE-A - PREPARATION OF THE BENZOFURANONE-INDOLYLOXAZOLE FRAGMENT

Authors
WIPF P YOKOKAWA F
Citation
P. Wipf et F. Yokokawa, SYNTHETIC STUDIES TOWARD DIAZONAMIDE-A - PREPARATION OF THE BENZOFURANONE-INDOLYLOXAZOLE FRAGMENT, Tetrahedron letters, 39(16), 1998, pp. 2223-2226
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
16
Year of publication
1998
Pages
2223 - 2226
Database
ISI
SICI code
0040-4039(1998)39:16<2223:SSTD-P>2.0.ZU;2-U
Abstract
The benzofuranone-indolyloxazole fragment of the polycyclic marine nat ural product diazonamide A was prepared from tryptamine. The oxazole r ing was synthesized from an alpha keto-indole via cyclodehydration wit h Ph3P/Cl3CCCl3, and after selective Stille biaryl coupling with 2-iod o-6-stannylphenol, the benzofuranone ring was constructed by an intram olecular Heck annulation of an alpha,beta-unsaturatedaryl ester. (C) 1 998 Elsevier Science Ltd. All rights reserved.