One-step spiroannulation. Synthesis of spiro. gamma.-and. delta.-lactones

P Canonne, D Belanger, G Lemay…

Index: Canonne, Persephone; Belanger, Denis; Lemay, Gilles; Foscolos, Georges B. Journal of Organic Chemistry, 1981 , vol. 46, # 15 p. 3091 - 3097

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Citation Number: 44

Abstract

Carbocyclic acid anhydrides can be converted to spiro y-and &lactones by addition of di- Grignard reagents in tetrahydrofuran solution. Five-and six-membered rings have been formed in one-step reactions. Possible mechanistic pathways for this reaction are discussed. The conversion of spirolactones to 1-(whydroxyalky1)-cycloalkanols was accomplished by reduction with LAH to illustrate the versatility of these substances giving (after or upon ...