A three-component coupling approach to cyclopentanoids.
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.
Trost
B M
BM
Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Pinkerton
A B
AB
D003517:Cyclopentanes / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
D003517:Cyclopentanes