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    • Asymmetric synthesis of a functionalized tricyclo[6.2.0.02,6]decane ring system present in kelsoene and poduran

      Amrita Ghosh Subrata Ghosh

      Regular Articles Volume 126 Issue 6 November 2014 pp 1875-1882

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      https://www.ias.ac.in/article/fulltext/jcsc/126/06/1875-1882

    • Keywords

       

      Asymmetric synthesis; cycloaddition; metathesis; terpenes.

    • Abstract

       

      Synthesis of a functionalized tricyclo[6.2.0.02,6]decane derivative in enantiomerically pure form, the core structure present in the natural products kelsoene and poduran, is described. The key steps involve a stereocontrolled copper (I)-catalyzed intramolecular [2+2] photocycloaddition of a 1, 6-diene prepared from D-mannitol to form a substituted bicyclo[3.2.0]heptane derivative and a ring closing olefin metathesis involving the vicinal substituents on the five-membered ring of the bicyclo[3.2.0]heptane derivative.

    • Author Affiliations

       

      Amrita Ghosh1 Subrata Ghosh1

      1. Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kolkata 700032, India

    • Dates

       
      Published
      November 2014
      Manuscript received
      27 February 2014
      Manuscript revised
      3 April 2014
      Accepted
      11 June 2014

    • Supplementary Material

       

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