Lissoclinolide, 1, which is an antibiotic butenolide isolated front a Tunicate, has been synthesized stereoselectively by a reaction sequence in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydroxy-2,6-octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross-coupling reaction of so obtained (Z)-2-bromo-5-[(E)-4-hydroxy-2-butenylidene]-5H-furan-2-one, (Z,E)-14, with (E)-3-hydroxyl-1-propenyltributylstannane, 15, have been used as the key steps. (C) 1998 Elsevier Science Ltd. All rights reserved.
Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization/cross-coupling reactions
ROSSI, RENZO;BELLINA, FABIO;
1998-01-01
Abstract
Lissoclinolide, 1, which is an antibiotic butenolide isolated front a Tunicate, has been synthesized stereoselectively by a reaction sequence in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydroxy-2,6-octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross-coupling reaction of so obtained (Z)-2-bromo-5-[(E)-4-hydroxy-2-butenylidene]-5H-furan-2-one, (Z,E)-14, with (E)-3-hydroxyl-1-propenyltributylstannane, 15, have been used as the key steps. (C) 1998 Elsevier Science Ltd. All rights reserved.File in questo prodotto:
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