Tetrahedron letters

Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization/cross-coupling reactions

R Rossi, F Bellina, M Biagetti, L Mannina

Index: Rossi, Renzo; Bellina, Fabio; Biagetti, Matteo; Mannina, Luisa Tetrahedron Letters, 1998 , vol. 39, # 42 p. 7799 - 7802

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Citation Number: 71

Abstract

Lissoclinolide, 1, which is an antibiotic butenolide isolated from a Tuncate, 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-hydroxy-1-propenyltributylstannane, 15 ...