Synthesis of a Novel, Highly Symmetric Bis-Oxa-Bridged Compound

Khan, Faiz Ahmed ; Dash, Jyotirmayee (2002) Synthesis of a Novel, Highly Symmetric Bis-Oxa-Bridged Compound Journal of the American Chemical Society, 124 (11). pp. 2424-2425. ISSN 0002-7863

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Official URL: http://doi.org/10.1021/ja017371f

Related URL: http://dx.doi.org/10.1021/ja017371f

Abstract

A highly oxygenated, novel pentacyclic bis-oxa-bridged compound 8 was synthesized with remarkable efficiency starting from readily available tetrachloro-5,5-dimethoxyclopentadiene and 1,4-cyclohexadiene in three steps. The ruthenium-catalyzed oxidation of 2:1 bis-adduct 1 followed by a one-pot transformation of the resulting bis-alpha-diketone 3 furnished (after esterification) the title compound in an overall yield of 29.1%. The versatility of this simple method was further demonstrated with other norbornyl alpha-diketones to obtain the corresponding strained oxa-bridged derivatives.

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Deposited On:17 Oct 2022 05:58
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