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Org Biomol Chem. 2013 Jun 14;11(22):3629-34. doi: 10.1039/c3ob27390c.

Highly stereoselective directed reactions and an efficient synthesis of azafuranoses from a chiral aziridine.

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1
Department of Chemistry, Sogang University, Seoul 121-742, Korea.

Abstract

Polyhydroxylated pyrrolidines, such as biologically important azafuranoses represented by the natural product (+)-2,5-imino-2,5,6-trideoxy-gulo-heptitol and its C(3)-epimer, were elaborated from a commercially available enantiomerically pure (2R)-hydroxymethylaziridine by highly stereoselective directed reactions in more than 61% overall yield. At first, the nucleophile 2-trimethylsilyloxyfuran was directed to (2R)-aziridine-2-carboxaldehyde by ZnBr2 to yield the unusual anti-addition product as a single isomer via the chelation-controlled transition. The ring opening of aziridine was followed by conjugate addition to give a cis-fused bicycle, which was converted to the target molecule after the required reductive operations.

PMID:
23538672
DOI:
10.1039/c3ob27390c
[Indexed for MEDLINE]
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