Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones.

نویسندگان

  • Santhosh Kumar Chittimalla
  • Hui-Yi Shiao
  • Chun-Chen Liao
چکیده

A novel and convenient approach, the domino retro Diels-Alder/Diels-Alder reaction sequence for highly stereo- and regioselective synthesis of various bicyclo[2.2.2]octenone and bicyclo[2.2.2]octadienone derivatives is presented. Thus, the masked o-benzoquinones (MOBs) 2a-e generated by the pyrolysis of the respective dimers 3a-e participated in this novel synthetic strategy with a variety of olefinic and acetylenic dienophiles at 220 degrees C to provide the title compounds in good to excellent yields.

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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 4 11  شماره 

صفحات  -

تاریخ انتشار 2006