Lipase enhanced catalytic efficiency in lactonisation reactions

We studied an enantioselective. lipase-catalysed transesterification reaction for the production of the statin lactone moiety. It is well known that the chiral cyclic structure of statins is very important for their pharmaceutical activity in the prevention and treatment of coronary artery diseases. We focused our attention on 3R,5R-6-(ethyl-2-phenyl)-4-hydroxytetrahydropyran-2-one (2); this was synthesised by employing an enantioselective lactonisation reaction catalysed by a commercial preparation of porcine pancreatic lipase (PPL) starting from a racemic mixture of syn-diol rac-1. Optimisation of the reaction conditions for the biocatalysed intramolecular transesterification reaction of the racemic diol I was carried out. It was seen that the maximal reaction rate could be greatly enhanced by the addition of solid matrices to the reaction medium. (C) 2001 Elsevier Science B.V. All rights reserved.