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J Org Chem

Title:		Stereoselective synthesis of trifluoro- and monofluoro-analogues of frontalin and evaluation of their biological activity
Author(s):		Ambrosi P; Arnone A; Bravo P; Bruche L; De Cristofaro A; Francardi V; Frigerio M; Gatti E; Germinara GS; Panzeri W; Pennacchio F; Pesenti C; Rotundo G; Roversi PF; Salvadori C; Viani F; Zanda M;
Address:		"CNR, Centro di Studio sulle Sostanze Organiche Naturali, via Mancinelli 7, I-20131 Milano, Italy"
Journal Title:		J Org Chem
Year:		2001
Volume:		66
Issue:		25
Page Number:		8336 - 8343
DOI:		10.1021/jo0055640
ISSN/ISBN:		0022-3263 (Print) 0022-3263 (Linking)
Abstract:		"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 beta-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"
Keywords:		"Animals Behavior, Animal/drug effects Bridged Bicyclo Compounds, Heterocyclic/*chemical synthesis/chemistry Coleoptera Electrophysiology Female Fluorine Indicators and Reagents Insect Control Pheromones/*antagonists & inhibitors/biosynthesis Sense Organs;"
Notes:		"MedlineAmbrosi, P Arnone, A Bravo, P Bruche, L De Cristofaro, A Francardi, V Frigerio, M Gatti, E Germinara, G S Panzeri, W Pennacchio, F Pesenti, C Rotundo, G Roversi, P F Salvadori, C Viani, F Zanda, M eng Research Support, Non-U.S. Gov't 2001/12/12 J Org Chem. 2001 Dec 14; 66(25):8336-43. doi: 10.1021/jo0055640"