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Synlett 1995; 1995(9): 918-920
DOI: 10.1055/s-1995-5124
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Stereoselective Radical Induced Cyclisation of Unsaturated Aldonolactones: Synthesis of Highly Functionalized, Enantiomerically Pure Cyclopentane Derivatives

Anne Marie Horneman, Inge Lundt* , Inger Søtofte
  • *Department of Organic Chemistry, Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark, Fax: +45 45 93 39 68
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Publication Date:
31 December 2000 (online)

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Radical induced cyclisation of ω-bromo-ω-deoxy-α,β-unsaturated aldonolactones using AIBN and Bu3SnH gave stereoselectively cyclopentane derivatives in high yields. The formation of a bicyclic system directs the trapping reagent to the less hindered side of the intermediate radical enolate (6 and 12), thus generating another new chiral center stereoselectively in 5 and 11. The lactone function in the products formed, i.e. 2, can be reduced to give an optically active cyclopentanetetraol 4, which might be viewed as a carbohydrate mimic.

Radical induced cyclisation - aldonolactones - optically active cyclopentane derivatives - sugar mimics