Preparation and Synthetic Applications of Phototropone
Jack P. Lowe, Nathan R. Halcovitch, S. C. Coote
Abstract
An optimized multigram-scale route to phototropone (bicyclo[3.2.0]hepta-2,6-dien-7-one) is reported via the 4-π-photocyclization of tropone complexed to Lewis acid. Phototropone is a highly versatile molecular building block, and its conversion into 18 novel derivatives using standard transformations is demonstrated, allowing access to a variety of rigid bicyclic scaffolds.
Topics & Concepts
ChemistryTroponeBicyclic moleculeBlock (permutation group theory)Combinatorial chemistryLewis acids and basesStereochemistryOrganic chemistryCatalysisMathematicsGeometryOxidative Organic Chemistry ReactionsSynthesis of Organic CompoundsSynthetic Organic Chemistry Methods