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dc.contributor.authorHudlicky, Tomas
dc.contributor.authorGoulart Stollmaier, Juana
dc.date.accessioned2020-02-07T19:58:11Z
dc.date.available2020-02-07T19:58:11Z
dc.date.issued2020-02-14
dc.identifier.citationGoulart Stollmaier, J.; Hudlický, T. Tetrahedron 2020, 76 (7), 130924.en_US
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/10464/14627
dc.description.abstractcis-Diene diol obtained from the microbial oxidation of bromobenzene was used as a substrate for the chemoenzymatic acetylation and epoxidation with lipases. The model studies showed that the regiochemistry of the acetylation is solvent-dependent. The chemoenzymatic epoxidation followed the expected regiochemistry when compared to the chemical epoxidation with m-CPBA, but with the unexpected formation of bromoconduritol-C, an important intermediate whose electrochemical reduction led to the synthesis of (-)-conduritol-C. Experimental and spectral data are provided for all new compounds.en_US
dc.description.sponsorshipthe Natural Sciences and Engineering Research Council of Canada (NSERC; Idea to Innovation and Discovery Grants), the Canada Research Chair Program, the Canada Foundation for Innovation (CFI), TDC Research, Inc., the TDC Research Foundation, the Ontario Partnership for Innovation and Commercialization (OPIC), and The Advanced Biomanufacturing Centre (Brock University).en_US
dc.language.isoen_USen_US
dc.publisherElsevieren_US
dc.relation.ispartofseriesTetrahedron;
dc.subjectenzymatic dihydroxylationen_US
dc.subjectlipasesen_US
dc.subjectacetylationen_US
dc.subjectepoxidationen_US
dc.subjectnarciclasineen_US
dc.subjectconduritol Cen_US
dc.titleSequential enzymatic and electrochemical functionalization of bromocyclohexadienediols: Application to the synthesis of (-)-conduritol Cen_US
dc.typeArticleen_US
dc.identifier.doi10.1016/j.tet.2020.130924
refterms.dateFOA2021-02-15T00:00:00Z


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