The Total Synthesis of dl-Quadrone

Article abstract of DOI:10.1021/ja00404a026

A regio- and stereospecific total synthesis of dl-quadrone (1) is described.The synthesis, which starts with 4,4-dimethylcyclopent-2-en-1-one (5), is accomplished in 19 steps in 3.1percent yield.The key intermediates are the enone ester 4, the iodo ketal 15, the tricyclic keto ester 16, and the hydroxymethyl keto acid 22.The latter as well as the seco acid 2 afford quadrone upon thermolysis.