Absolute configuration of aromatic oxygenated isoprenoid derivatives: formation of 3-hydroxy-4,4-dimethyl-4-butyrolactone by ozonolysis and a study of its stereochemistry

Abstract

Ozonolysis of the hydroxyisopropylfuroquinoline alkaloid, platydesminium metho-salt, afforded (+)-3-hydroxy-4,4-dimethyl-4-butyrolactone. The structure of the lactone was established by asymmetric synthesis of its formate ester and its absolute configuration by correlation with (–)-4-methylpentane-1,3-diol.