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 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.