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

Abstract

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 delta-lactones mixture showed significant antinociceptive properties in preliminary tests using the tail flick model assay.

DOI: 10.1016/j.bioorg.2010.05.001

Cite this paper

@article{Miranda2010StructuralDV, title={Structural determination Vitex cymosa Bertero active principle: Diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one and its antinociceptive activity.}, author={Leandro S de Maris e Miranda and Bruno Guimar{\~a}es Marinho and Jeronimo da Silva Costa and Suzana Guimar{\~a}es Leit{\~a}o and Tereza Cristina dos Santos and Franco Delle Monache and Patricia Dias Fernandes and M{\'a}rio Luiz Ara{\'u}jo de Almeida Vasconcellos and Vera L{\'u}cia Patrocinio Pereira}, journal={Bioorganic chemistry}, year={2010}, volume={38 5}, pages={181-5} }