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

Article abstract of DOI:10.1016/S0040-4039(98)01705-5

Lissoclinolide, 1, which is an antibiotic butenolide isolated from 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-hydroxy-1-propenyltributylstannane, 15, have been used as the key steps.