New Polyhydroxylated Pyrrolidines Derived from Enantiopure 3,6-Dihydro-2H-1,2-oxazines

Diastereoselective hydroborations of enantiopure 3,6-dihydro-2H-1,2-oxazines led to dihydroxy-substituted 1,2-oxazines. Samarium diiodide-induced N−O bond cleavage generated 1,4-amino alcohols which were recyclized to polyhydroxylated pyrrolidines which are potential glycosidase inhibitors.

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Bibliographic Details
Published in:Organic letters 2002-07, Vol.4 (14), p.2353-2355
Main Authors: Pulz, Robert, Al-Harrasi, Ahmed, Reissig, Hans-Ulrich
Format: Article
Language:English
Online Access:Get full text
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Description
Summary:Diastereoselective hydroborations of enantiopure 3,6-dihydro-2H-1,2-oxazines led to dihydroxy-substituted 1,2-oxazines. Samarium diiodide-induced N−O bond cleavage generated 1,4-amino alcohols which were recyclized to polyhydroxylated pyrrolidines which are potential glycosidase inhibitors.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0260573