title: A three-component coupling approach to cyclopentanoids.
abstract: A new approach to 2,3-disubstituted cyclopentenones has been developed. This approach consists of a two-step protocol involving the cyclization of a Z-vinyl bromide under Barbier type conditions to form a cyclopentenol, which is then oxidatively rearranged to generate the cyclopentenone. The Z-vinyl bromide is in turn derived from a ruthenium catalyzed three-component coupling of an alkyne, an enone, and a HBr equivalent. A range of 2,3-disubstituted cyclopentenones has been generated, including short syntheses of jasmone and dihydrojasmone. Further applicability of this strategy is shown in the total syntheses of tetrahydrodicranenone B, rosaprostol, and a selective COX-2 inhibitor.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
authors.forename: B M
authors.initials: BM
authors.lastname: Trost
authors.forename: A B
authors.initials: AB
authors.lastname: Pinkerton
mesh_terms: D003517:Cyclopentanes / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D003517:Cyclopentanes