Collect. Czech. Chem. Commun. 1989, 54, 1683-1686

Large-scale synthesis of racemic “Corey lactone”

Ivan Veselýa, Václav Kozmíkb, Václav Dědekb, Jaroslav Palečekb, Jiří Mosteckýb and Ivan Stiborc

a Research and Development Division, Chemical Works Spolana, 277 11 Neratovice
b Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
c Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Very convenient synthesis of Corey lactone–(3aα,4α,5β,6aα)-5-(1,1'-biphenyl-4-carbonyloxy)-hexahydro-4-hydroxymethyl-2H-cyclopenta[b]furan-2-one (VI) was developed. The title compound was obtained in five steps starting from 7-anti-hydroxymethyl-5-exo-chloro-bicyclo[2.2.1]-heptan-2-one (I) in a very good overall yield.