863128-54-5Relevant academic research and scientific papers
First asymmetric synthesis of (+)-sordidin and (-)-7-epi-sordidin, aggregation pheromones of the banana weevil cosmopolites sordidus
Enders, Dieter,Breuer, Irene,Nuehring, Anja
, p. 2677 - 2683 (2005)
The asymmetric synthesis of (1S,3R,5R,7S)-(+)-sordidin and 7-epi-(1S,3R,5R,7R)-(-)-sordidin, both components of the natural male-produced aggregation pheromone of the banana weevil Cosmopolites sordidus (Germar), starting from 2,2-dimethyl-1,3-dioxan-5-one is described. Two of the stereogenic centers were generated by three α-alkylations of the corresponding RAMP-hydrazone. Diastereoselective epoxide opening as another key step of the synthesis employing the aza-enolate of 3-pentanone SAEP-hydrazone as nucleophile and subsequent acidic intramolecular acetalisation furnished the sordidin C-7 epimers in good overall yield (39%) as a 1.5:1 diastereomeric mixture. The epimers could be separated by preparative GC and thus, each of them could be obtained in high diastereomeric and enantiomeric purity (de ≥ 97%, ee ≥ 98%).
