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Regiospecific Michael reaction of (+)-euryfuran with activated 1,4-benzoquinones

✍ Scribed by Jaime A Valderrama; Manuel Cortés *; David Pessoa-Mahana; Marcelo Preite; Julio Benites

Book ID
104210261
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
107 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

+)-Euryfuran cycloadds regiospecifically to activated monosubstituted 1,4-benzoquinones under mild conditions to give the corresponding Michael adducts which, depending on the quinone substituent, undergo in situ redox reactions to the respective euryfurylbenzoquinones. One of the reported Michael adducts undergoes a facile stereoselective cyclisation under oxidant conditions to afford a naphthofuro[4,3-c]benzopyran derivative. The regiospecificity of the Michael and cyclisation reactions are discussed.

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