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Issue 0, 1986
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Synthesis and rearrangements of the pentacyclo[5.4.0.0.0.0]undecane [1,2,4-trishomocubane] ring system

Abstract

Two syntheses of the pentacyclo[5.4.0.02,6.03,10.04,8]undecane (1,2,4-trishomocubane) system are described. The first synthesis involves intramolecular photochemical [2 + 2]-cycloaddition of the triquinane bisenones (14ad) to furnish the 1,2,4-trishomocubanediones (15ad). The second approach is based on a boron trifluoride–diethyl ether-catalysed rearrangement of the readily available Cookson's caged diketones (16a,b) to 1,2,4-trishomocubanediones (17a,b). Thermal and acid-catalysed [2 + 2]-cycloreversions of (15a,c,d) and (17a,b) to linear fused triquinanes (14a,c,d), (20a,b) and tricyclo[5.3.1.02,6]undecane systems of current synthetic interest are also described.

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Article type: Paper
DOI: 10.1039/P19860000291
Citation: J. Chem. Soc., Perkin Trans. 1, 1986,0, 291-297

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    Synthesis and rearrangements of the pentacyclo[5.4.0.0.0.0]undecane [1,2,4-trishomocubane] ring system

    G. Mehta, A. V. Reddy and A. Srikrishna, J. Chem. Soc., Perkin Trans. 1, 1986, 0, 291
    DOI: 10.1039/P19860000291

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