Structural determination Vitex cymosa Bertero active principle: Diastereoselective synthesis of (±)- trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one and its antinociceptive activity

The synthesis of (±)- δ-lactone 2 allowed the elucidation of the correct structure of Vitex cymosa Bertero active principle. The (±)- δ-lactone showed significant antinociceptive properties in preliminary tests using the tail flick model assay. The diastereoselective synthesis of (±)- trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one, as a mixture trans:cis (3:1), was accomplished using a protocol that combine the Prins cyclization and RuO 4 oxidation. The synthesis this lactone allowed the elucidation of the correct structure of the substance isolated from the barks of Vitex cymosa. The δ-lactones mixture showed significant antinociceptive properties in preliminary tests using the tail flick model assay.