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Synthesis 1997; 1997(5): 509-511
DOI: 10.1055/s-1997-1228
DOI: 10.1055/s-1997-1228
short paper
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An Enantiocontrolled Synthesis of Both Enantiomers of Frontalin
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synthesis/199705/lookinside/thumbnails/10.1055-s-1997-1228-1.jpg)
Both (+)- and (-)-enantiomers of frontalin, the aggregation pheromone of the Dendroctonus pine beetles, have been synthesized in an enantiocontrolled way from 2-acetyl-5-methylfuran by use of the Sharpless asymmetric dihydroxylation and the oxidative ring-expansion reactions as key steps.
frontalin - insect pheromone - asymmetric dihydroxylation - oxidative furan-ring expansion - chiral 6,8-dioxabicyclo[3.2.1]octance ring system