Tetrahedron

Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with …

…, C Dartiguelongue, D Séraphin, JM Oger, P Richomme

Index: Helesbeux, Jean-Jacques; Duval, Olivier; Dartiguelongue, Caroline; Seraphin, Denis; Oger, Jean-Michel; Richomme, Pascal Tetrahedron, 2004 , vol. 60, # 10 p. 2293 - 2300

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Citation Number: 30

Abstract

Application of our original photooxidation–reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2- hydroxy-3-methylbut-3-enyl) phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising ...