Studies in terpenoids. Part XXIII. An approach to the 1-aryl-1,2,2-trimethylcyclopentane skeleton by intramolecular ketocarbene insertion. Synthesis of β-cuparenone
Abstract
The 1-aryl-1,2,2-trimethylcyclopentane system, which contains the carbon skeleton of many cuparenoids, can be prepared by intramolecular ketocarbene insertion in the benzylic C(5)–H bond of a 5-aryl-1-diazo-4,4-dimethyl-hexan-2-one. β-Cuparenone (3,4,4-trimethyl-3-p-tolylcyclopentanone) has been synthesised in this way.