An Improved Synthesis of (±)Frullanolide. Application of Selenium Reagents

A new approach to the total synthesis of (±)Frullanolide (1), employing selenium reagents, is described. This methodology has significant advantages over our previously reported synthesis in that (a) the construction of the α-methylene-γ-lactone moiety is made in such a manner to avoid the formation of undesirable stereo- and regioisomers; (b) the synthesis was performed in 7 steps, starting from known octalone 2, with an overall yield of 27%.