The Journal of Organic Chemistry

Directed metalation of N, N-diethylbenzamides. Silylated benzamides for the synthesis of naturally occurring peri-methylanthraquinones and peri-methyl polycyclic …

RJ Mills, V Snieckus

Index: Mills, Robert J.; Snieckus, Victor Journal of Organic Chemistry, 1989 , vol. 54, # 18 p. 4386 - 4390

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Citation Number: 24

Abstract

Efficient methodologies based on directed ortho metalation, fluoride-induced carbodesilylation, and metal-halogen exchange processes (Scheme I) are reported for the synthesis of peri-methyl-substituted anthraquinone natural products 5 and polycyclic aromatic hydrocarbons 6, 7. Benzamide 8 (Scheme 11) is converted in a one-pot sequence into the disilylated derivative 10, which upon metalation, condensation with 3, 5- ...