| Abstract: | The synthesis of a new compound with a sanddalwood odour is described. The synthesis of the lactone1 has been designed by molecular considerations: a bicyclus with a side chain containing 5–7 carbon atoms and an oxygene containing osmophoric group. One route to synthesize1 leads from the ketone3 via theMannich base4 to the  -ketonitrile6 which after hydrolysis to the -keto acid7 and reduction of the latter cyclises spontaneously to1. A shorter route starts from the  -bromoketone13 which could be transformed by malonic ester synthesis into7. Other synthetic routes, e.g. cyanoethylation to the homologous  -lactone16 aldol condensation, alkylation, carboxymethylation and carboxyethylation of3 failed as well as the preparation of the oxazoline protected 3-bromopropionic acid for aGrignard synthesis with3. 1 exhibits a sweet, warm odour, of sandalwood with an interesting note of cedarwood.Teil der Diplomarbeit vonSchindler, K., Universität Wien, 1979. |
