Organic letters

Intramolecular Direct Dehydrohalide Coupling Promoted by KO t Bu: Total Synthesis of Amaryllidaceae Alkaloids Anhydrolycorinone and Oxoassoanine

S De, S Ghosh, S Bhunia, JA Sheikh, A Bisai

Index: De, Subhadip; Ghosh, Santanu; Bhunia, Subhajit; Sheikh, Javeed Ahmad; Bisai, Alakesh Organic Letters, 2012 , vol. 14, # 17 p. 4466 - 4469

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Citation Number: 73

Abstract

A transition-metal-free intramolecular dehydrohalide coupling via intramolecular homolytic aromatic substitution (HAS) with aryl radicals has been developed in the presence of potassium tert-butoxide and an organic molecule as the catalyst. The methodology has been applied to a concise synthesis of Amaryllidaceae alkaloids viz. oxoassoanine (1b), anhydrolycorinone (1d), and other related structures. Interestingly, the method also works ...