Canadian Journal of Chemistry p. 872 - 880 (1982)
Update date:2022-08-04
Topics:
McKay, William R.
Ounsworth, Jim
Sum, Phaik-eng
Weiler, Larry
(+/-)-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.
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Doi:10.1021/ja00381a049
(1982)Doi:10.1016/j.carres.2004.09.010
(2004)Doi:10.1007/BF00913844
(1952)Doi:10.1016/S0040-4039(00)87059-8
(1982)Doi:10.1016/S0040-4039(00)87053-7
(1982)Doi:10.1021/acs.jafc.9b03606
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