Abstract
The diastereoselective synthesis of (S )-4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)butan-1-ol (9 ), an intermediate in the asymmetric synthesis of the pine beetle pheromone (-)-frontalin [(1S ,5R )-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane] (1 ), has been accomplished starting from the β-keto sulfoxide 2 , derived from glutaric anhydride. The key step of the synthetic sequence is the diastereoselective hydrocyanation of 2 by diethylaluminum cyanide.
Key words
asymmetric synthesis - frontalin - diastereoselective hydrocyanation - chiral cyanohydrins - β-keto sulfoxides
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