ChemInform Abstract: Asymmetric Synthesis of Both Enantiomers of α,α-Difluoroeldanolide: An Interesting Property of Their Biological Activity.

✍ Scribed by T. ITOH; K. SAKABE; K. KUDO; P. ZAGATTI; M. RENOU

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 40 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199834284

✦ Synopsis

Asymmetric Synthesis of Both Enantiomers of α,α-Difluoroeldanolide: An Interesting Property of Their Biological Activity.

-The synthesis of (4R,5R)-α,α-difluoroeldanolide (IX), a fluorinated analogue of a sex pheromone of the male African sugarcane borer, is prepared from the enantiopure (R)-allylic alcohol (I) via radical cyclization of the acetal (VII) as key step. The corresponding (4S,5S)-enantiomer is obtained from (S)-(I) by the same sequence. Dose-response curves show the difluorinated analogues to be as active as the natural pheromone. -(ITOH, T.;