71899-15-5Relevant academic research and scientific papers
Synthesis of (+/-)-lineatin by the photochemical cycloaddition of allene to anhydromevalonolactone
McKay, William R.,Ounsworth, Jim,Sum, Phaik-eng,Weiler, Larry
, p. 872 - 880 (2007/10/02)
(+/-)-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.
