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  • Title: Highly stereoselective radical cyclization of haloacetals controlled by the acetal center.
    Author: Villar F, Kolly-Kovac T, Equey O, Renaud P.
    Journal: Chemistry; 2003 Apr 04; 9(7):1566-77. PubMed ID: 12658655.
    Abstract:
    A systematic investigation of radical haloacetal cyclizations (Ueno-Stork reaction) where the acetal center is the unique stereogenic element is reported. This highly diastereoselective reaction can be used for the preparation of polysubstituted tetrahydrofurans and gamma-lactones. We report herein the full experimental details of reactions where up to three new chiral centers are created. To demonstrate the potential of this approach, short syntheses of (+)-eldanolide and of tricyclic acetals related to biologically active lignans have been achieved.
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