Studies directed toward the total synthesis of tetronolide 2. A stereoselective route to the racemic cyclohexene subunit

Article abstract of DOI:10.1016/S0040-4039(00)79872-8

A short stereo selective sequence is described for the preparation of the racemic form of the highly functionalized cyclohexene derivative 2 which comprises the upper segment of tetronolide (1), the aglycone of the antitumor tetrocarcins. A key element of this route is rapid assembly and intramolecular cycloaddition of the trienyl enol pyruvate 4, which achieves complete control over regiochemistry and good stereochemical control.