Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 9, Issue 7, Pages 1566-1577Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200390180
Keywords
asymmetric synthesis; cyclizations; haloacetals; lactones; radical reactions
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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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