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Paper | Special issue | Vol 88, No. 2, 2014, pp.1255-1274
Published online, 27th August, 2013
DOI: 10.3987/COM-13-S(S)89
Chemoenzymatic Approach to Synthesis of Hydroxylated Pyrrolidines from Benzoic Acid

David R. Adams, Johannes van Kempen, Jason R. Hudlicky, and Tomas Hudlicky*

*Department of Chemistry, Brock University, 500 Glenridge Ave., St. Catharines, Ontario, L2R 3K4, Canada


The fermentation of benzoic acid with R. eutrophus B9 provides the corresponding ipso-diol that serves as a convenient homochiral starting material for the synthesis of oxygenated compounds. In this paper we report the conversion of the ipso-diol to a hydroxylated pyrrolidine, which is found as a subunit in biologically active compounds. The key steps involve the enzymatic oxidation of benzoic acid, the subsequent hetero-Diels-Alder cycloaddition, and the oxidative cleavage, reductive cyclization to form the pyrrolizidine. Experimental and spectral data are provided for all new compounds.