Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization

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 therapeuti...

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Veröffentlicht in:Tetrahedron 2009-06, Vol.65 (26), p.4957-4967
Hauptverfasser: Struble, Justin R., Bode, Jeffrey W.
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Bode, Jeffrey W.
description 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. [Display omitted]
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subjects Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
title Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization
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