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Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization.

ABSTRACT: An N-heterocyclic carbene (NHC) catalyzed intramolecular lactonization to prepare densely functionalized bicyclic ?-lactam-?-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.

SUBMITTER: Struble JR

PROVIDER: S-EPMC2896295 | biostudies-literature | 2009 Jun

REPOSITORIES: biostudies-literature

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Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization.

Struble Justin R JR Bode Jeffrey W JW

Tetrahedron 20090601 26

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. ...[more]

PMID: 20606761

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