Chemoenzymatic synthesis of (+)-aspicilin from chlorobenzene.
The enantiomerically pure cis-1,2-dihydrocatechol 2, which is obtained by microbial oxidation of chlorobenzene, has been converted, via intermediate 3, into the natural product (+)-aspicilin (1).
Banwell
M G
MG
Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia.
McRae
K J
KJ
D002396:Catechols / Q000138:chemical synthesis / Q000737:chemistry; D002722:Chlorobenzenes / Q000737:chemistry*; D004926:Escherichia coli / Q000201:enzymology / Q000235:genetics; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010105:Oxygenases; D013237:Stereoisomerism
D002396:Catechols; D002722:Chlorobenzenes; D007202:Indicators and Reagents; D007783:Lactones; C418323:aspicilin; D010105:Oxygenases; C023172:toluene dioxygenase; C031294:chlorobenzene