Tetrahedron

Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization

JR Struble, JW Bode

Index: Struble, Justin R.; Bode, Jeffrey W. Tetrahedron, 2009 , vol. 65, # 26 p. 4957 - 4967

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Citation Number: 48

Abstract

An N-heterocyclic carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic γ-lactam-γ-lactone adducts from enals is reported. This method has been applied to the formal synthesis of salinosporamide A, a potent 20S proteasome inhibitor and anti-cancer therapeutic.