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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/100/02-03/0223-0234

    • Keywords

       

      Dodecahedrane; C2v-tetraquinane dione; cis-Hexaquinane; bis-cyclopentannulation; cyclopentanone inversion

    • 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.

    • Author Affiliations

       

      Goverdhan Mehta1 K Raja Reddy1 Mangalam S Nair1

      1. School of Chemistry, University of Hyderabad, Hyderabad - 500134, India
    • Dates

       
  • Journal of Chemical Sciences | News

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