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Michael-Type Adducts of 3-Carbethoxycoumarins via Diels-Alder Reaction: Tandem Ring Construction of Furopyranochroman-2-one Skeletons

  作者 PRABHAKAR MADDELA; REDDY G NARENDAR; SRINU G; MANJULATHA K; PRASAD J VENKATA; KUMAR S PRAMOD; SRINIVAS O; IQBAL JAVED; KUMAR K ANIL  
  选自 期刊  SYNLETT;  卷期  2010年-6;  页码  947-951  
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[摘要]Diels-Alder reaction of furan with electron-deficient 3-carbethoxycoumarins gave the Michael-type adducts obtained from the rearrangement of the intermediate Diels-Alder adducts, instead of the Diels-Alder cycloadducts. Trapping of the dipolar intermediate with electron-deficient aromatic aldehydes gave a one-pot access to fused furo[3,2-b]pyranochroman-2-ones with multiple stereogenic centers. Ring opening of the lactone moiety gave a facile route to generate diverse scaffolds.

 
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