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Free-radical reactions of carbohydrate derivatives in the synthesis of carbocyclic compounds

2. Conversion of 3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo[2.2.1]heptanes into the corresponding cyclopentane derivatives

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Abstract

The decisive influence of the carboxyl group on the methanolysis of 3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo[2.2.1.]heptanes was proved experimentally, and several routes of conversion of the latter to the corresponding cyclopentanes were found.

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References

  1. A. F. Sviridov and N. K. Kochetkov,Izv. Akad. Nauk, Ser. Khim., 1992, 650 [Bull. Acad. Sci., Div. Chem. Sci., 1992,41, 511 (Engl. Transl.)].

  2. R. A. Alonso, G. D. Vite, R. E. MeDevitt, and B. Fraser-Reid,J. Org. Chem., 1992, 573.

  3. A. F. Sviridov, D. V. Yashunskii, M. S. Ermolenko, V. S. Borodkin, and N. K. Kochetkov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1166 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 1066 (Engl. Transl.)].

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For Communication 1 see Ref.1

This work was partially supported by the Russian Foundation for Fundamental Research.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1989–1991, November, 1993.

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Sviridov, A.F., Frolov, A.B. & Kochetkov, N.K. Free-radical reactions of carbohydrate derivatives in the synthesis of carbocyclic compounds. Russ Chem Bull 42, 1906–1908 (1993). https://doi.org/10.1007/BF00699015

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  • DOI: https://doi.org/10.1007/BF00699015

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