Publication details

Synthesis of trihydroxylated pyrrolizidine using 1,3-dipolar cycloaddition of D-erythrose derived nitron

Authors

KUBÁŇ Juraj KOLAROVIČ Alex FIŠERA Ĺubor JÄGER Volker HUMPA Otakar PRONAYOVÁ Naďa

Year of publication 2001
Type Article in Periodical
Magazine / Source Synlett
MU Faculty or unit

Central European Institute of Technology

Citation
Description 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

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