Microbiological transformations 57. Facile and efficient resin-based in situ SFPR preparative-scale synthesis of an enantiopure "unexpected" lactone regioisomer via a Baeyer-Villiger oxidation process.
[reaction: see text] The microbiological Baeyer-Villiger oxidation of (-)-bicyclo[3.2.0]hept-2-en-6-one allowed exclusive formation of the "unexpected" lactone regioisomer in 84% yield, high chemical purity, and enantiopure form. Substrate (25 g) was transformed in a 1 L bubble column reactor, following a in situ substrate feeding/product removal methodology, which afforded high volumetric productivity (1.2 g L(-)(1) h(-)(1)). This illustrates the high "sustainable chemistry" advantages of such a process, simply conducted in aqueous medium, at room temperature and using atmospheric oxygen.
Hilker
Iris
I
Groupe Biocatalyse et Chimie Fine, UMR CNRS 6111, Université de la Méditerranée, Faculté des Sciences de Luminy, Case 901, 163 avenue de Luminy, 13288 Marseille Cedex 9, France.
Gutiérrez
María C
MC
Alphand
Véronique
V
Wohlgemuth
Roland
R
Furstoss
Roland
R
D019149:Bioreactors; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis*; D004926:Escherichia coli / Q000378:metabolism; D007218:Industrial Microbiology / Q000379:methods; D007783:Lactones / Q000138:chemical synthesis* / Q000378:metabolism; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D012117:Resins, Synthetic / Q000737:chemistry*; D013237:Stereoisomerism; D013997:Time Factors
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; D007783:Lactones; D012117:Resins, Synthetic; C419322:bicyclo(3,2,o)hept-3-en-6-one