Complexity-Enhancing Acid-Promoted Rearrangement of Tricyclic Products of Tandem Ugi 4CC/Intramolecular Diels-Alder Reaction

摘要

The unexpected rearrangement of 2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1-one products of the tandem Ugi 4CC/ intramolecular Diels-Alder reaction in 85% H_3PO_4 was discovered to provide diastereomerically pure tricyclic bis-lactam lactone-containing natural product-like products in high yield.Mechanistic rationale for the observed rearrangement was proposed and has been tentatively confirmed by additional experiments.