title: Ugi and Passerini reactions of biocatalytically derived chiral aldehydes: application to the synthesis of bicyclic pyrrolidines and of antiviral agent telaprevir.
abstract: Lipase mediated desymmetrization of a meso-diol (1,2-cyclopentanedimethanol) allows the synthesis of both enantiomers of some chiral aldehydes, whose behavior in Passerini and Ugi reactions has been explored. Exploiting these two complementary multicomponent reactions and coupling them with a subsequent cyclization process, we observed that 6 out of all 8 possible stereoisomers of peptidomimetic pyrrolidines can be obtained in good yields. The potential of these protocols has been proved by the development of a new efficient synthesis of antiviral drug telaprevir.
authors: †Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy.
authors: Lisa
authors: L
authors: Moni
authors: †Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy.
authors: Luca
authors: L
authors: Banfi
authors: †Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy.
authors: Andrea
authors: A
authors: Basso
authors: ‡Chemessentia Srl, via Bovio 6, 28100 Novara, Italy.
authors: Luca
authors: L
authors: Carcone
authors: ‡Chemessentia Srl, via Bovio 6, 28100 Novara, Italy.
authors: Marcello
authors: M
authors: Rasparini
authors: †Department of Chemistry and Industrial Chemistry, University of Genova, via Dodecaneso 31, 16146 Genova, Italy.
authors: Renata
authors: R
authors: Riva
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry; D055162:Biocatalysis; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008049:Lipase / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000998:Antiviral Agents; D019086:Bridged Bicyclo Compounds, Heterocyclic; D009842:Oligopeptides; D011759:Pyrrolidines; C486464:telaprevir; D008049:Lipase