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Cyclization of isoprenoid compounds

Communication 9. Stereospecific cyclization of geranylacetic acid, its methyl ester, and its monocyclic analogs
  • A. V. Semenovskii
  • V. A. Smit
  • V. F. Kucherov
Organic and Biological Chemistry

Summary

  1. 1.

    Under the conditions of the acid-catalyzed (H2SO4) low-temperature cyclization of geranylacetic acid and its cyclic analogs there occurs the stereospecific formation of isomeric bicyclic δ -lactones, the configuration of which may be determined both by the cis-trans isomerism of the original geranylacetic acid and by the position of the double bond (α or β) in the cyclogeranylacetic acid.

     
  2. 2.

    The cyclization of geranylacetic esters and their monocyclic analogs goes via an intermediate complex, the decomposition of which with an anhydrous base leads to cyclogeranylacetic esters and the decomposition of which with water leads to δ -lactones, the formation of which also goes stereospecifically.

     
  3. 3.

    A scheme is proposed for the mechanism of the transformations studied.

     

Keywords

Ester Double Bond H2SO4 Lactone Isoprenoid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau Enterprises Inc. 1965

Authors and Affiliations

  • A. V. Semenovskii
    • 1
  • V. A. Smit
    • 1
  • V. F. Kucherov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of SciencesUSSR

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