Enantioselective syntheses of isoprostane and iridoid lactones intermediates by enzymatic transesterification

Crude Pseudomonas cepacia lipase (Amano PS-30) is a suitable biocatalyst fo r the kinetic resolution of the 1,2-cis-disubstituted cyclopentanoid buildi ng block (3aR*,4R*,6aS*)-(+/-)-4-hydroxymethyl-3,3a,4,6a-tetrahydrocyclopen ta[b]furan-2-one through enantioselective transesterification. Enantiomeric ally enriched acetic acid (3aS,4S,6aR)-(+)-2-oxo-3,3a,4,6a-tetrahydro2H-cyc lopenta[b]furan-4-yl methyl ester was utilized in a formal synthesis of the iridoids (+)-isoiridomyrmecin and (-)-teucrium-lactone. (C) 2001 Elsevier Science Ltd. All rights reserved.