Synthesis based on cyclohexadienes. Part 35: Synthesis of some polyquinane derivatives

Abstract

A new strategy for the synthesis of a [4.3.3]propellane derivative and an angular triquinane is described starting from the tetracyclic compounds 8 and 15. The synthesis of the [4.3.3]propellane involved a radical cyclisation and a Beckmann fragmentation as the key steps. The angular triquinane was synthesised employing an oxidative cleavage of the tetracyclic system. A novel Wilkinson’s catalyst-mediated carbon–carbon bond formation (12 → 30) is reported.