摘要 |
<p>New process for preparing the pheromone active compound lineatin (3,3,7-trimethyl-2,9-dioxatricyclo AD3,3,1,04,7 BD-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 AD3,2,0 BDheptan-3-one derivative of formula (4) is subjected to oxidation; the resulting 5,5,9-trimethyl-2,6-dioxa-7-oxo-bicyclo AD4,2,0 BDoctylspiro AD2,7 BD-decane derivative of formula (5) is subjected to oxidation; the resulting 1,5,5-trimethyl-4-oxabicyclo AD4,2,0 BD-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. </p> |