| Abstract
| - A new approach to 2,3-disubstituted cyclopentenones has been developed. This approach consistsof a two-step protocol involving the cyclization of a Z-vinyl bromide under Barbier type conditionsto form a cyclopentenol, which is then oxidatively rearranged to generate the cyclopentenone. TheZ-vinyl bromide is in turn derived from a ruthenium catalyzed three-component coupling of analkyne, an enone, and a HBr equivalent. A range of 2,3-disubstituted cyclopentenones has beengenerated, including short syntheses of jasmone and dihydrojasmone. Further applicability of thisstrategy is shown in the total syntheses of tetrahydrodicranenone B, rosaprostol, and a selectiveCOX-2 inhibitor.
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