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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Bibliographic Details
Published in:	Tetrahedron Vol. 65; no. 26; pp. 4957 - 4967
Main Authors:	Struble, Justin R., Bode, Jeffrey W.
Format:	Journal Article Conference Proceeding
Language:	English
Published:	Kidlington Elsevier Ltd 27-06-2009 Elsevier
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 Intramolecular reaction Catalytic reaction Nitrogen heterocycle Lactam Lactone Malignant tumor Enaldehyde Oxygen heterocycle Functionalization Proteasome inhibitor Proteasome endopeptidase complex Bicyclic compound Lactonization Chemical synthesis Cancer
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Summary:	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]
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	0040-4020 1464-5416
DOI:	10.1016/j.tet.2009.03.103