Tetrahedron

Exploration of conjugate addition routes to advanced tricyclic components of mangicol A

S Pichlmair, M de Lera Ruiz, I Vilotijevic, LA Paquette

Index: Pichlmair, Stefan; de Lera Ruiz, Manuel; Vilotijevic, Ivan; Paquette, Leo A. Tetrahedron, 2006 , vol. 62, # 24 p. 5791 - 5802

Full Text: HTML

Citation Number: 18

Abstract

Two synthetic approaches to the cytotoxic marine natural product known as mangicol A are described. The starting material common to both pathways is the cyclopentenonecarboxylate 11. The first tactic involves the 1, 4-addition to 11 of the cuprate derivable from iodide 10, while the second proceeds via base-promoted conjugate addition of the regiospecifically generated enolate anion of 41. The first strategy proceeds by a ...