G. Zanoni et al., Enantioselective syntheses of isoprostane and iridoid lactones intermediates by enzymatic transesterification, TETRAHEDR-A, 12(12), 2001, pp. 1779-1784
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
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