Halogenated cannabinoid synthesis

Abstract

A convenient synthesis of several tricyclic and bicyclic fluoro- and iodo analogs of cannabinoids has been reported. A new, mild methodology for the synthesis of vinyl fluorides from vinylstannanes has also been demonstrated. These C9 halo-functionalized cannabinoid analogs, along with (−) and (+)-Δ 9-THC carboxylic acids, were screened for anti-inflammatory activity in the mouse ear edema assay. It was interesting to find that both enantiomers of Δ 9-THC carboxylic acid were moderately active as anti-inflammatories. The bicyclic vinyl iodide ( 18C) also showed appreciable anti-inflammatory activity.