Ricardo Callejoand David O'Hagan
EaStCHEM, University of St. Andrews, School of Chemistry, St. Andrews, Fife, KY16 9ST, UK
There has been a long interest in the molecular basis of perfumes and fragrance and particularly the relationship of molecular shape to the olfactory response . Some of the most iconic fragrances are the macrocyclic musk odorants, such a muscone, civetone or dihydrocivetone, which are highly aliphatic and display significant conformational freedom. Unfortunately, the exact mechanism by these compounds activate olfactory receptors is still unclear.
Our research group has developed a conformational tool based onto the unique ability of CF2 groups to occupy corner locations in a macrocycle . As an extension of this programme, we have designed a set of fluorinated civetone analogues, containing the gem-difluoromethylene motif in strategic locations, to reinforce or distort the overall shape of this 17-membered ketone. The synthesis and structure-odour  relationships of different fluorinated analogues will be discussed in this talk .
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 Cambridge, 2006. (b) Rossiter, K.J. Chem. Rev. 1996, 96, 3201.
 (a) Corr, M.J.; Cormanich, R.A.; Von Hahmann, C.N.; Bühl, M.; Slawin, A.M.Z.; O'Hagan, D. Org. Biomol. Chem. 2016, in press. (b) Skibinski, M.; Urbina-Blanco, C.A.; Slawin, A.M.Z.; Nolan, S.P.; O'Hagan, D. Org. Biomol. Chem. 2013, 11, 8209. (c) Skibinski, M.; Wang, Y.; Slawin, A.M.Z.; O'Hagan, D. Angew. Chem. Int. Ed. 2011, 50, 10581.
 Assessed at Givaudan Schweiz AG, Dübendorf, Switzerland.