Synthesis of a New Spirolactone: 7,10-Dimethoxy-1-oxaspiro[4,5]deca-6,9-diene-2,8-dione


  •  Guy Plourde    
  •  Mark D. Fairchild    
  •  Gurkaran S. Sarohia    

Abstract

The title compound was synthesized in 36 % yield by oxidative spiroannulation of the corresponding 2,4,5-trisubstituted phenol. Interestingly, this phenol was prepared in 57 % yield from another spirocompound, namely 7-methoxy-1-oxaspiro[4,5]deca-6,9-diene-2,8-dione. We have speculated that the formation of the phenol was due to a series of reactions involving a conjugate addition of methanol to the original spirolactone followed by aromatization and lactone hydrolysis.



This work is licensed under a Creative Commons Attribution 4.0 License.
  • ISSN(Print): 1916-9698
  • ISSN(Online): 1916-9701
  • Started: 2009
  • Frequency: semiannual

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