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Synlett 1998; 1998(12): 1378-1380
DOI: 10.1055/s-1998-1966
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Synthesis of (+/-)-Oxohexahydrofuro[3,2-b]pyrroles (Pyrrolidine-trans-lactones) via a Reduction-Alkylation Protocol

Simon J. F. Macdonald* , John G. Montana, Doreen M. Buckley, Michael D. Dowle
  • *Enzyme Chemistry II, GlaxoWellcome Medicines Research Centre, Gunnels Wood Road, Stevenage, SG1 2NY, UK; Fax + (0) 1438 763 616
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Publication Date:
31 December 2000 (online)

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A synthesis of pyrrolidine-trans-lactones is described commencing from 1-(benzyloxycarbonyl)-3-oxo-2-pyrrolidineacetic acid ethyl ester. cis-Reduction of the oxo-pyrrolidine followed by hydroxyl inversion with benzoic acid in a Mitsunobu reaction gave the trans-benzoate ester which was converted into its corresponding silyl ether. After allylation α to ethyl ester, silyl deprotection, saponification and trans-lactonisation gave pyrrolidine-trans-lactones. Stereoselective allylation of trans-1-(benzyloxycarbonyl)-3-hydroxy-2-pyrrolidine-acetic acid ethyl ester is feasible to give predominantly the desired diastereomer.

pyrrolidine-trans-lactone - acyl-iminium - ketene acetal - bromohydrin diol