STEREOCONTROLLED SYNTHESIS OF LISSOCLINOLIDE BY SEQUENTIAL TRANSITION-METAL-CATALYZED LACTONIZATION CROSS-COUPLING REACTIONS/

Authors
ROSSI R BELLINA F BIAGETTI M MANNINA L
Citation
R. Rossi et al., STEREOCONTROLLED SYNTHESIS OF LISSOCLINOLIDE BY SEQUENTIAL TRANSITION-METAL-CATALYZED LACTONIZATION CROSS-COUPLING REACTIONS/, Tetrahedron letters, 39(42), 1998, pp. 7799-7802
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
42
Year of publication
1998
Pages
7799 - 7802
Database
ISI
SICI code
0040-4039(1998)39:42<7799:SSOLBS>2.0.ZU;2-Q
Abstract
Lissoclinolide, 1, which is an antibiotic butenolide isolated front a Tunicate, has been synthesized stereoselectively by a reaction sequenc e in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydr oxy-2,6-octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross -coupling reaction of so obtained o-5-[(E)-4-hydroxy-2-butenylidene]-5 H-furan-2-one, (Z,E)-14, with (E)-3-hydroxyl-1-propenyltributylstannan e, 15, have been used as the key steps. (C) 1998 Elsevier Science Ltd. All rights reserved.