Synthesis of (+/-)-lineatin by the photochemical cycloaddition of allene to anhydromevalonolactone

Article abstract of DOI:10.1139/v82-131

(+/-)-Lineatin (1), the aggregation pheromone of an ambrosia beetle, was synthesized in five steps from anhydromevalonolactone (5) in 10percent overall yield.The key step in the synthesis was a photochemical cycloaddition of 5 and allene.This photolysis produced two regioisomers (ca. 3:2) and efforts to improve the regioselectivity by varying the photolysis conditions or substituents on the allene were unsuccessful.