Tetrahedron letters

Synthetic studies toward the immunosuppressant FR901483. Facile construction of the azatricyclic skeleton

STM Simila, A Reichelt, SF Martin

Index: Simila, Suvi T. M.; Reichelt, Andreas; Martin, Stephen F. Tetrahedron Letters, 2006 , vol. 47, # 17 p. 2933 - 2936

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Citation Number: 20

Abstract

A concise synthesis of the azatricyclic core structure of FR901483, a potent immunosuppressant, has been accomplished. The key elements of the approach involve a nucleophilic addition to an acyl iminium ion, a ring closing metathesis and a lactone–lactam rearrangement to provide the tricyclic structure.