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Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone

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Abstract

A new method for the synthesis of (1R,4S,5S)-4-hydroxymethyl-3-oxabicyclo[3.1.0]hexan2-one, the cyclopropane analog of (S)-5-hydroxypent-2-en-4-olide, has been suggested based on oxidation of (1S,2S,4R,6R)-7,9-dioxatricyclo[4.2.1.02,4]nonan-5-one. Oxidation of cyclobutanones, spirojoined with the fragments of 6,8-dioxabicyclo[3.2.1]oct-2-ene, 6,8-dioxabicyclo[3.2.1]octane (at position 4), or 7,9-dioxatricyclo[4.2.1.02,4]nonane (at position 5), upon the action of m-chloroperoxybenzoic acid or the KMnO4-H2SO4-H2O system leads to the corresponding spirojoined butanolides in 73–85% yields. The same cyclobutanones easily undergo the four-membered ring opening upon the action of dilute H2SO4 at 50–90 °C to form 6,8-dioxabicyclo[3.2.1]octane-4- or 7,9-dioxatricyclo[4.2.1.02,4]nonane-5-propionic acid.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    R. A. Novikov, R. R. Rafikov, E. V. Shulishov & Yu. V. Tomilov

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  1. R. A. Novikov
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  2. R. R. Rafikov
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  3. E. V. Shulishov
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  4. Yu. V. Tomilov
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Correspondence to Yu. V. Tomilov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1880–1886, October, 2010.

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Novikov, R.A., Rafikov, R.R., Shulishov, E.V. et al. Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone. Russ Chem Bull 59, 1930–1936 (2010). https://doi.org/10.1007/s11172-010-0336-4

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  • DOI: https://doi.org/10.1007/s11172-010-0336-4

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