Abstract
An intramolecular carbocyclization was found of levoglucosenone adduct with isoprene providing a fused cyclobutane. The intramolecular oxacyclization of the adduct was performed under the treatment with I2, H3PO4, SOCl2, and Pd/C leading to 1,4-epoxide. Methods were developed of radical and anionic (by Ferrier method) transformation of the adduct into chiral trans- and cis-decalins.
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Original Russian Text © B.T. Sharipov, O.Yu. Krasnoslobodtseva, L.V. Spirikhin, F.A. Valeev, 2009, published in Zhurnal Organicheskoi Khimii, 2010, Vol. 46, No. 2, pp. 232–241.
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Sharipov, B.T., Krasnoslobodtseva, O.Y., Spirikhin, L.V. et al. Reactions of stereocontrolled intramolecular carbocyclization of levoglucosenone adduct with isoprene. Russ J Org Chem 46, 226–235 (2010). https://doi.org/10.1134/S1070428010020144
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DOI: https://doi.org/10.1134/S1070428010020144