Enantioselective syntheses of isoprostane and iridoid lactones intermediates by enzymatic transesterification

• Published in: Tetrahedron: asymmetry Vol. 12; no. 12; pp. 1779 - 1784
• Main Authors: Zanoni, Giuseppe, Agnelli, Fabio, Meriggi, Alessia, Vidari, Giovanni
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 16.07.2001; Elsevier
• Subjects: Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Chemistry, Physical; Physical Sciences; Science & Technology; KINETIC RESOLUTION; ENZYMES; (+)-ISOIRIDOMYRMECIN; MONOTERPENE LACTONES
• ISSN: 0957-4166; 1362-511X
• DOI: 10.1016/S0957-4166(01)00311-1

Crude Pseudomonas cepacia lipase (Amano PS-30) is a suitable biocatalyst for the kinetic resolution of the 1,2- cis-disubstituted cyclopentanoid building block (3a R*,4 R*,6a S*)-(±)-4-hydroxymethyl-3,3a,4,6a-tetrahydrocyclopenta[ b]furan-2-one through enantioselective transesterification. Enantiomerically enriched acetic acid (3a S,4 S,6a R)-(+)-2-oxo-3,3a,4,6a-tetrahydro-2 H-cyclopenta[ b]furan-4-yl methyl ester was utilized in a formal synthesis of the iridoids (+)-isoiridomyrmecin and (−)-teucriumlactone. Enzymatic resolution of (±)- 1 by acylation with Pseudomonas cepacia lipase (Amano PS-30) afforded (+)- 1 and (+)- 2 with e.e. of ≥95%. Acetate (+)- 2 was utilized in a formal synthesis of the iridoids (+)-isoiridomyrmecin and (−)-teucriumlactone.