Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation Suzuki Miyaura cross coupling strategy

…, S Brown, P Hodson, V Snieckus

Index: Cai, Xiongwei; Brown, Stephen; Hodson, Peter; Snieckus, Victor Canadian Journal of Chemistry, 2004 , vol. 82, # 2 p. 195 - 205

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Citation Number: 32

Abstract

Using a combined directed ortho metalation (DoM) Suzuki Miyaura cross coupling directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl-(5a), 1, 7- dimethyl-(5b), 2, 7-dimethyl-(5c), 7-ethyl-1-methyl-(15), and 7-tert-butyl-1- methylphenanthrenes (27) have been synthesized in four to seven steps and 21% 36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram ...