Tetrahedron

Evaluation of possible intramolecular [4+ 2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antiinflammatory agent mangicol A

S Pichlmair, M de Lera Ruiz, K Basu, LA Paquette

Index: Pichlmair, Stefan; de Lera Ruiz, Manuel; Basu, Kallol; Paquette, Leo A. Tetrahedron, 2006 , vol. 62, # 22 p. 5178 - 5194

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Citation Number: 17

Abstract

A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels–Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1, 3- diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any ...

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