Cannabis XVIII. Isolation and synthesis of olivetol derivatives formed in the pyrolysis of cannabidiol

Article abstract of DOI:10.1002/recl.19780970704

Pyrolysis of cannabidiol results in the formation of several new cannabinoids and cracking products. In an earlier paper several structures were proposed for the cracking products based on GCMS measurements. In this paper the isolation and synthesis of the majority of these cracking products - which are in general C₂-substituted olivetol derivatives - is described. 2,6-Dimethoxy-4-pentylphenyl-lithium and the cuprates derived therefrom proved to be very promising intermediates for the synthesis of olivetol derivatives specifically substituted at C₂. The versatility of these reagents is illustrated by several examples.