Synthesis of (+/-)-lineatin by the photochemical cycloaddition of allene to anhydromevalonolactone
(+/-)-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.
McKay, William R.,Ounsworth, Jim,Sum, Phaik-eng,Weiler, Larry
p. 872 - 880
(2007/10/02)
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