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Trends in Heterocyclic Chemistry   Volumes    Volume 3 
Abstract
Studies on the syntheses of oxygen-containing cyclic compounds
Sadao Tsuhoi
Pages: 199 - 210
Number of pages: 12
Trends in Heterocyclic Chemistry
Volume 3 

Copyright © 1993 Research Trends. All rights reserved

ABSTRACT
 
This review describes new syntheses of oxygen containing cyclic compounds such as epoxides, furans, γ-butyrolactones, butenolides, δ-alkylidene-δ-lactones, and tetraoxo-adamantanes. Almost of the present works were carried out in the author`s laboratory. A new synthesis of selenophene, furan related compound, is also described. Optically active α,β-epoxyalcohols were obtained in good yields with high optical purities by the reduction of α-chloroketones with bakers` yeast as a key step. Novel synthesis of furans and selenophenes by the oxidation of conjugated dienoates with selenium oxide is reported. A new synthesis of γ-lactones by the thermal treatment of γ-halo esters with silica gel is described. Convenient syntheses of α,γ-disubstituted butenolides via debromination-dealkoxycarbonylation with Nal and optically active butenolides by the reduction of β-chloro- γ-oxoalkanoates with bakers` yeast as a key step are reviewed. δ-Alkoxycarbonylethylidene-δ-lactones were prepared by Wittig reaction of dicarboxylic anhydrides. Syntheses of several natural products such as (-)-disparlure, 14,15-leukotriene A4, (±)-canadensolide, santonin related compound, (±)-acarenoic acid, (-)- avenaciolide are described.
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