Tetrahedron

Cyclisation and subsequent reactions of 2′-hydroxy-6′-methoxychalcone epoxide and related compounds

CJ Adams, L Main

Index: Adams, Christopher J.; Main, Lyndsay Tetrahedron, 1991 , vol. 47, # 27 p. 4979 - 4990

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Citation Number: 18

Abstract

2′-Hydroxy-6′-methoxychalcone epoxide reacts in neutral aqueous acetonitrile solution to give a 6: 1 ratio of the α-and β-cyclisation products, erythro-4-methoxyaurone hydrate [erythro-2-(α-hydroxybenzyl)-4-methoxycoumaran-3-one] and trans-3-hydroxy-5- methoxyflavanone: the dominance of α-cyclisation may be associated with a stereoelectronic preference for a conformation favourable for α-but not β-cyclisation when ...