Process for the preparation of lineatin

Details Process for the preparation of lineatin Process for the preparation of lineatin

C - Chemistry, Metallurgy

07

D

260/353.8

C07D 491/18 (2006.01) C07C 29/38 (2006.01) C07C 45/29 (2006.01) C07C 45/67 (2006.01) C07C 45/71 (2006.01) C07C 47/21 (2006.01) C07C 49/203 (2006.01) C07C 49/653 (2006.01) C07D 311/76 (2006.01) C07D 493/08 (2006.01) C07D 493/10 (2006.01)

Patent

CA 1198441

ABSTRACT New process for preparing the pheromone active compound lineatin (3,3,7-trimethyl-2,9-dioxatricyclo[3,3,1,04'7]- nonane), by reacting a 2,2-dimethyl-3,4-pentadienal of formula 1, in which R1 and R2 is each hydrogen or lower alkyl, with .beta.-methylallyl magnesium halide; the formed 2,5,5- trimethylocta-1,6,7-trien-4-ol derivative of formula 2 is subjected to oxidation which does not attack the double bonds; the formed 2,5,5-trimethylocta-1,6,7-trien-4-one derivative of formula 3 is subjected to pyrolysis; the formed 1,4,4- trimethyl-6-methylenebicyclo[3,2,0]heptan-3-one derivative of formula 4 is subjected to oxidation; the resulting 5,5,9-trimethyl-2,6-dioxa-7-oxo-bicyclo[4,2,0]octylspiro[2,7]- decane derivative of formula 5 is subjected to oxidation; the resulting 1,5,5-trimethyl-4-oxabicyclo[4,2,0]-octan-3,7- dione of formula 6 is reduced in a per se known manner to lineatin of formula 7. Compounds 2, 3, 4 and 5 are novel. Image Image 3 4 Image Image Image 6 7

449142

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