FACILE ACCESS TO 4-ARYL-2(5H)-FURANONES BY SUZUKI CROSS-COUPLING - EFFICIENT SYNTHESIS OF RUBROLIDE-C AND RUBROLIDE-E

Authors
BOUKOUVALAS J LACHANCE N OUELLET M TRUDEAU M
Citation
J. Boukouvalas et al., FACILE ACCESS TO 4-ARYL-2(5H)-FURANONES BY SUZUKI CROSS-COUPLING - EFFICIENT SYNTHESIS OF RUBROLIDE-C AND RUBROLIDE-E, Tetrahedron letters, 39(42), 1998, pp. 7665-7668
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
42
Year of publication
1998
Pages
7665 - 7668
Database
ISI
SICI code
0040-4039(1998)39:42<7665:FAT4BS>2.0.ZU;2-5
Abstract
The Pd(0)-catalyzed cross coupling between 4-bromo-2(5H)-furanones and arylboronic acids provides the corresponding 4-aryl-2(5H)-furanones i n yields of 61-85%. By using this method in conjunction with furanolat e chemistry, the marine antibiotics rubrolide C and E have been synthe sized in highly efficient fashion (4 steps, overall yield = 61 and 56% respectively) from beta-tetronic acid. (C) 1998 Elsevier Science Ltd. All rights reserved.