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.
Format:	Artikel
Sprache:	eng
Schlagworte:	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
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Beschreibung
Zusammenfassung:	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]
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2009.03.103