An efficient enzymatic synthesis of benzocispentacin and its new six- and seven-membered homologues.
A very efficient enzymatic method was developed for the synthesis of new enantiomeric benzocispentacin and its six- and seven-membered homologues through the Lipolase (lipase B from Candida antarctica) catalyzed enantioselective (E > 200) ring opening of 3,4-benzo-6-azabicyclo[3.2.0]heptan-7-one, 4,5-benzo-7-azabicyclo[4.2.0]octan-8-one, and 5,6-benzo-8-azabicyclo[5.2.0]nonan-9-one with H2O in iPr2O at 60 degrees C. The (1R,2R)-beta-amino acids (ee > or = 96%, yields > or = 40%) and (1S,6S)-, (1S,7S)-, and (1S,8S)-beta-lactams (ee > 99%, yields > or = 44%) produced could be easily separated. The ring opening of racemic and enantiomeric beta-lactams with 18% HCl afforded the corresponding beta-amino acid hydrochlorides.
Forró
Eniko
E
Institute of Pharmaceutical Chemistry, University of Szeged, 6701 Szeged, PO Box 121, Hungary.
Fülöp
Ferenc
F
D001555:Benzene Derivatives / Q000138:chemical synthesis*; D005656:Fungal Proteins; D008049:Lipase / Q000378:metabolism*; D008722:Methods; D004369:Pentetic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001555:Benzene Derivatives; D005656:Fungal Proteins; D004369:Pentetic Acid; D008049:Lipase; C431349:lipase B, Candida antarctica