Synthesis of densely functionalized pyrrolidinone templates by an intramolecular oxo-Diels–Alder reaction

Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered tha...

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Bibliographic Details
Published in:Tetrahedron letters 2002-10, Vol.43 (41), p.7389-7392
Main Authors: Murray, William V., Mishra, Pranab K., Sun, Sengen, Maden, Amy
Format: Article
Language:English
Subjects:
intramolecular hetero Diels–Alder reaction
pyrrolidinone
remote hydroxylation
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Summary:Preparation of densely functionalized pyrrolidinone templates, is a challenge for synthetic chemists. These templates are important building blocks for novel conformationally constrained natural products or for library generation of highly functionalized bi or polycyclic compounds. We discovered that trienes 6a– j undergo facile stereoselective intramolecular Diels–Alder reactions to generate densely functionalized cis fused pyrrolidinone templates 1a– j . These reactions allow for directed remote hydroxylation with complete control of stereochemistry. A series of highly functionalized pyrrolidinones was prepared by an intramolecular oxo Diels–Alder reaction and further elaborated to hydroxy ketones by enol ether hydrolysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01711-2