Abstract
Isopatchoul-9-en-5α-ol (VII) was hydrogenated using nickel catalyst in methanol to give 10α (H)-isopatchoulan-5α-ol (XII). Dehydration of the alcohol (XII) formed 10-epi-cyperene (IV) which on oxidation yielded 10-epi-cyperotundone (V). The alcohol (VII) was converted into 9α-acetoxy-10α (H)-isopatchoul-4-ene (XVII) via 10α (H)-isopatchoulane-5α, 9α-diol (XIV) by known methods. Hydrolysis of the unsaturated acetate (XVII) afforded 10α (H)-isopatchoul-4-en-9α-ol (XIX) which was oxidized to yield isopatchoul-4-en-9-one (XXI). Wolff-Kishner reduction of the ketone (XXI) furnished cyperene (III) which on oxidation gave cyperotundone (I) and patchoulenone (II).
