281193-46-2Relevant academic research and scientific papers
Stereoselective synthesis of trifluoro- and monofluoro-analogues of frontalin and evaluation of their biological activity
Ambrosi,Arnone,Bravo,Bruche,De Cristofaro,Francardi,Frigerio,Gatti,Germinara,Panzeri,Pennacchio,Pesenti,Rotundo,Roversi,Salvadori,Viani,Zanda
, p. 8336 - 8343 (2001)
The stereoselective synthesis of both enantiomers of trifluoro frontalin (-)-(1S,5R)- and (+)-(1R,5S)-8, as well as of diastereomeric monofluoro frontalines (-)- (1R,2R,5R)-18 and (-)-(1R,2S,5R)-20, analogues of the bioactive component of the aggregation pheromone of the Scolytidae insect family, has been accomplished starting from (-)-(1R)- and (+)-(1S)-menthyl (S)-toluene-4-sulfinate as a source of chirality and methyl trifluoroacetate or fluoroacetate, respectively, as sources of fluorine. The C-1 stereocenters were installed via stereoselective epoxidation of β-sulfinyl ketones 2 and 13 with diazomethane. The bicyclic core was obtained by totally stereocontrolled and chemoselective tandem Wacker oxidation/intramolecular ketalization of the intermediate unsatured sulfinyl diols 5, 15, and 19. Axially fluorinated (-)-20 elicited a strong electroantennographic response in laboratory tests on females of Dendroctonus micans, whereas equatorially fluorinated (-)-18 and the trifluoroanalogue (-)-8 showed modest responses. Field trials using (-)-20 were not indicative owing to the locally scarce population of D. micans, but it showed some attractiveness for other Coleoptera families.
Synthesis of 2-fluoro analogues of frontalin
Bravo, Pierfrancesco,Frigerio, Massimo,Ono, Taizo,Panzeri, Walter,Pesenti, Cristina,Sekine, Akiko,Viani, Fiorenza
, p. 1387 - 1389 (2007/10/03)
The synthesis of enantiomerically and diastereomerically pure (-)- (1R,2R,5R)- and (-)-(1R,2S,5R)-2-fluoro frontalin (7) starting from (+)-(1S)- menthyl-(R)-toluene-4-sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4-pentenyl bromide and diazome
