Total synthesis of (+)-dactylol via a novel [3 + 5] annulation approach

Article abstract of DOI:10.1021/jo00119a038

(+)-Dactylol (1) has been synthesized from the known (R)-3-methyl-2-methylenecyclopentanone (20) in six steps. The key step in the synthesis involves a regioselective and stereoselective [3 + 5] annulation to afford a tricyclic ether, which upon suitable functional group manipulation was opened to provide the natural product.