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Synthetic studies in quest of Platonic hydrocarbon dodecahedrane

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Abstract

In pursuit of Platonic hydrocarbon dodecahedrane1, a retrosynthetic theme indicated in scheme 1, was formulated. The precursor tetraquinanedione synthon5 was first designed through a photo-thermal olefin metathesis approach. The tetraquinanedione 5 was further elaborated toexo, exo-tetraquinane diester15 through carbonyl homologation, oxidation, esterification sequence, scheme 5. Bis-cyclopentannulation ofexo,exo-diester15 by Greene methodology delivered a functionalised C20-hexaquinane44, havingexo-annulated cyclopentane rings. Cyclopentane inversion was achieved by a set of reactions involving enone generation, double bond isomerisation and hydrogenation to give spheroidal (C2v)-C20-hexaquinanedione-diester47, the penultimate precursor of dodecahedrane 1. Several interesting transformations and rearrangements of polyquinanes are also described.

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Authors and Affiliations

  1. School of Chemistry, University of Hyderabad, 500134, Hyderabad, India

    Goverdhan Mehta, K. Raja Reddy & Mangalam S. Nair

Authors
  1. Goverdhan Mehta
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  2. K. Raja Reddy
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  3. Mangalam S. Nair
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Additional information

IUPAC nomenclature: Undecacyclo[9.9.0.02,9.03,7.04,20.05,18.06,16.08,15.010,14.012,19.013,17]eicosane.

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Mehta, G., Reddy, K.R. & Nair, M.S. Synthetic studies in quest of Platonic hydrocarbon dodecahedrane. Proc. Indian Acad. Sci. (Chem. Sci.) 100, 223–234 (1988). https://doi.org/10.1007/BF02839450

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