1067938-41-3Relevant academic research and scientific papers
Formal synthesis of (-)-frontalin through diastereoselective hydrocyanation of a β-keto sulfoxide
Ortiz, Benjamin,Sanchez-Obregon, Ruben,Toscano, Ruben A.,Yuste, Francisco
experimental part, p. 2105 - 2109 (2009/04/03)
The diastereoselective synthesis of (S)-4-(2,2,4-trimeth-yl-l,3-dioxolan-4- yl)butan-l-ol (9), an intermediate in the asymmetric synthesis of the pine beetle pheromone (-)-frontalin [(1S,5R)-l,5-dimethyl-6,8-dioxabicyclo[3.2.1] octane] (1), has been accomplished starting from the ss-keto sulfoxide 2, derived from gl-utaric anhydride. The key step of the synthetic sequence is the diastereoselective hydrocyanation of 2 by diethylaluminum cyanide. Thieme Stuttgart.
