• Studies in terpenoids. Part 43: Synthesis of (±)-2,6-dimethyl-10-(p-tolyl) undeca-2,6 (E)-diene, the diterpene ofSalvia dorisiana

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      https://www.ias.ac.in/article/fulltext/jcsc/087/08/0235-0238

    • Keywords

       

      Diterpene; Salvia dorisiana ; synthesis by one pot reaction; geranylacetone; citrylidene-p-methylacetophenone

    • Abstract

       

      (±)-2, 6-Dimethyl-10-(p-tolyl) undeca-2,6(E)-diene (1a), a diterpene hydrocarbon from the essential oil ofSalvia dorisiana has been synthesised by two methods. One pot reaction ofp-tolylmagnesium bromide with geranylacetone (5) and hydrogenolysis of the resulting benzylic alcohol (1b) without isolation furnished the natural product (1a). In the other method citrylidene-p-methylacetophenone (6a) was used as the starting material. The trienone (6a) was reduced to the corresponding alcohol (6b) which was hydrogenated to (6c) and oxidised to the dienone (6d). Reaction of the dienone (6d) with methylmagnesium jdoide, followed by dehydration of the carbinol and reduction with lithium in liquid ammonia furnished the diterpene (1a).

    • Author Affiliations

       

      T K John1 2 G S Krishna Rao1

      1. Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012
      2. Department of Chemistry, Southeastern Massachusetts University, North Dortmouth - MAO 2747, USA
    • Dates

       
  • Journal of Chemical Sciences | News

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