Synthesis of (±)-campherenone, (±)-epicampherenone, (±)-β-santalene, (±)-epi-β-santalene, (±)-α-santalene, (±)-ylangocamphor, (±)-copacamphor, and (±)-sativene

Abstract

The completion of part of a general synthetic route to sesquiterpene analogues of camphor, bornan-2-ol, camphene and tricyclene is illustrated by an alternative total synthesis of campherenone and epicampherenone [the epimeric 1,7-dimethyl-7-(4-methylpent-3-enyl)norbornan-2-ones], β-santalene and epi-β-santalene [2-methyl-3-methylene-2-(4-methylpent-3-enyl)norbornanes], α-santalene {1,7-dimethyl-7-(4-methylpent-3-enyl)tricyclo-[2.2.1.0^2,6]heptane}, and the perhydro-1,4-methanoindene derivatives copacamphor, ylangocamphor, and sativene.