Approaches to the Syntheses of Acorone and Lycopodine

PART I Various attempts to synthesise acorone, or a mixture of two or more of the three possible isomeric acorones, acorone, isoacorone and cryptoacorone, are described. The course of the synthesis was successful up to a late stage, but attempts either to Introduce an isopropyl group into 4-ethoxycarbonyl-1,7-dimethylspiro(5,4)decan-3,6-dione, or to effect internal cyclisation of ethyl 2-isopropyl-5-(4-methyl-5-oxocyclohex-l(6)-enyl)-3-oxohexanoate, proved fruitless; if either of these reactions had been accomplished, a compound with the gross structure of acorone would have been readily obtainable. The feasibility of the synthetic route was proven by the facile synthesis of desisopropylacorone