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  • Title: Stereoselective synthesis of sugar fused β-disubstituted γ-butyro-lactones: C-spiro-glycosides from 1,2-cyclopropanecarboxylated sugars.
    Author: Sridhar PR, Seshadri K, Reddy GM.
    Journal: Chem Commun (Camb); 2012 Jan 18; 48(5):756-8. PubMed ID: 22134500.
    Abstract:
    A stereoselective methodology was developed for the construction of C-spiro-glycosides in two steps involving bromonium ion activated solvolytic ring opening of sugar derived 1,2-cyclopropanecarboxylates followed by a one-pot dehydrohalogenation, intramolecular hetero-Michael addition (IHMA) and ester hydrolysis. The obtained spirocyclic lactols were further converted to enantiomerically pure spirolactones.
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