Synthesis of (+/-)-Lineatin, an Aggregation Pheromone of Trypodendron lineatum

Article abstract of DOI:10.1021/ja00384a040

A regioselective synthesis of lineatin (1) was accomplished, starting from anhydromevalonolactone (8).Photochemical cycloaddition of 8 with acetylene gave the cyclobutene 9, which was converted to lactone 13 upon methylation followed by oxidation.Hydroboration-oxidation of 13 afforded a mixture of 14 and 15, from which tosylate 18 was obtained.Reduction of 18 gave the endo hemiacetal 19, which underwent an intramolecular displacement to produce 1.Isolineatin (2) was obtained by reduction of 13 to hemiacetal 20, followed by intramolecular oxymercuration with mercuric pivalate and reduction with sodium borohydride.