Synthesis of trihydroxylated pyrrolizidine using 1,3-dipolar cycloadditionof D-erythrose derived nitrone

Authors
Kuban, J Kolarovic, A Fisera, L Jager, V Humpa, O Pronayova, N
Citation
J. Kuban et al., Synthesis of trihydroxylated pyrrolizidine using 1,3-dipolar cycloadditionof D-erythrose derived nitrone, SYNLETT, (12), 2001, pp. 1866-1868
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
2001
Pages
1866 - 1868
Database
ISI
SICI code
0936-5214(200112):12<1866:SOTPU1>2.0.ZU;2-X
Abstract
A route has been developed for the synthesis of enantiomerically and diaste reomerically pure trihydroxylated pyrrolizidines. A chiral sugar derived ni trone undergoes diastereoselective dipolar cycloaddition with methyl acryla te to afford erythro-cis isoxazolidine a suitable cycloadduct undergoes N-O cleavage and recyclization to (1S.2R.6R.7aS)-trihydroxylated pyrrolizidine .