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Synlett 2001; 2001(12): 1866-1868
DOI: 10.1055/s-2001-18783
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Synthesis of Trihydroxylated Pyrrolizidine using 1,3-Dipolar Cycloaddition of d-Erythrose Derived Nitrone

Juraj Kubáň* , Andrej Kolarovič, Lubor Fišera, Volker Jäger, Otakar Humpa, Nada Prónayová
  • *Department of Organic Chemistry, Slovak University of Technology, SK-812 37 Bratislava, Slovak Republic; E-mail: fisera@cvt.stuba.sk
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Publication Date:
04 December 2001 (online)

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A route has been developed for the synthesis of enantiomerically and diastereomerically pure trihydroxylated pyrrolizidines. A chiral sugar derived nitrone undergoes diastereoselective dipolar cycloaddition with methyl acrylate to afford erythro-cis isoxazolidine; a suitable cycloadduct undergoes N-O cleavage and recyclization to (1S,2R,6R,7aS)-trihydroxylated pyrrolizidine.

cycloadditions - nitrones - isoxazolidines - stereoselectivity - pyrrolizidine alkaloid