Transannular Diels-Alder model studies on the total synthesis of chatancin. The furanophane approach. Part 1: Assembly of the acyclic substrates

Abstract

Synthesis of three generations of model substrates with advancing similarity to chatancin are presented. In the first two generations, an Ireland-Claisen based six-step sequence supplied the trans-dienophile to be connected by dithiane chemistry to furfurals. In the third generation, a homogeraniol based dienophile aldehyde was coupled with a dilithiated 3-furoic acid. Subsequently, all three generations were concluded with similar functional group modifications as a preparation for a malonate-furyl chloride based macrocyclization.