• Synthesis of natural triisopentenylated flavanone, euchrenone a2

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    • Keywords

       

      Tri-isopentenylated chalcone; tri-isopentenylated flavanone; euchrenone a2

    • Abstract

       

      Euchrenone a2 (7) isolated from the roots ofEuchresta japonica has been synthesised from 3-prenylphloroacetophenone (1) by other workers. We carried out its cyclodehydrogenation with dichloro dicyano quinone (DDQ) to obtain 6-acetyl-5,7-dihydroxy-2,2-dimethylchromene (2) which was ethoxymethylated in the 7-position to give 6-acetyl-7-ethoxymethoxy-5-hydroxychromene (3). Chalcone condensation of3 and 4-ethoxymethoxy-3-C-prenylbenzaldehyde (4) gave 4,6′-bisethoxymethoxy-2′-hydroxy-6″, 6″-dimethyl-3-C-prenylpyrano (2″, 3″–4,3) chalcone (5) which cyclised with methanolic sodium acetate to give protected 5,4′-bisethoxymethoxy-6″, 6″-dimethyl-3′-C-prenylpyrano (2″, 3″–7,8) flavanone (6). Deprotection of6 with 4% methanolic HCl yielded (7) with melting point and spectral data identical to that of the natural compound.

    • Author Affiliations

       

      Amolak C Jain1 Ashok K Prasad1

      1. Department of Chemistry, University of Delhi, Delhi - 110 007, India
    • Dates

       
  • Journal of Chemical Sciences | News

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