Efficient Synthesis Of Beetle Aggregation Pheromone Frontalin And Its Analogues

(1S,5R)-(-)-Frontalin is an aggregation pheromone secreted from thesouthern pine beetle (Dendroctonus frontalis), the western pine beetle (Dendroctonus brevicomis), and the Douglas-fir beetle (Dendroctonus pseudotsugae). It possesses the aggregation activity and has found application in selective exterminating of certain harmful insects while imposing minimal environmental impact. Because of the relatively simple structure containing a 6,8-dioxabicyclo[3.2.1]octane framework and the unique bioactivity, both non-asymmetric and asymmetric syntheses of frontalin have drawn tremendous attention in the synthetic community. Remarkably, efficient assembly of this pheromone remains a great challenge. Now we wish to disclose an expedite synthesis of (+)-frontalin and (-)-frontalin starting from a symmetric diene, via a one-flask operation consisting of double dihydroxylation, wo玱-cleavage, and acid-catalyzed intramolecular acetalation. Our unique strategy was also successfully applied to additional diene substrates .Xiaobao Yang (Organic Chemistry) Directed by Chengwen Hua, Hongbin Zhai...