Synthesis of (±)-lineatin by the photochemical cycloaddition of allene to anhydromevalonolactone
- 1 April 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (7) , 872-880
- https://doi.org/10.1139/v82-131
Abstract
(.+-.)-Lineatin, the aggregation pheromone of an ambrosia beetle [Trypodendron lineatum], was synthesized in 5 steps from anhydromevalonolactone (5) in 10% overall yield. The key step in the synthesis was a photochemical cycloaddition of 5 and allene. This photolysis produced 2 regioisomers (.apprx. 3:2) and efforts to improve the regioselectivity by varying the photolysis conditions or substituents on the allene were unsuccessful.This publication has 3 references indexed in Scilit:
- Lineatin: regioselective synthesis and resolution leading to the chiral pheromone of Trypodendron lineatumThe Journal of Organic Chemistry, 1980
- Synthesis and field testing of 4,6,6-lineatin, the aggregation pheromone ofTrypodendron lineatum (Coleoptera: Scolytidae)Journal of Chemical Ecology, 1979
- Isolation and tentative identification of lineatin, a pheromone from the frass ofTrypodendron lineatum (Coleoptera: Scolytidae)Journal of Chemical Ecology, 1977