A NEW SYNTHESIS OF LINEATIN, THE PHEROMONE OF TRYPODENDRON LINEATUM

Abstract

Trypodendronlineaturn Olivier is a serious pest in European forests. A new synthesis of (±)-, (+) - and (-)-lineatin (3,3,7-trimethyl-2,9-dioxatricyclo [3.3.1.04.7] nonane, 1) was achieved avoiding the use of photo-cycloaddition which was the key-step in our previous synthesis. By this a large-scale preparation of (±)-lineatin became possible. The stereochemistry of the bioactive (+)-lineatin was established as IR, 4S, 5R, 7R by an X-ray crystallographic analysis of an intermediate.