General route to anthraquinone natural products via directed metalation of N, N-diethylbenzamides

SO De Silva, M Watanabe…

Index: de Silva,S.O. et al. Journal of Organic Chemistry, 1979 , vol. 44, # 26 p. 4802 - 4808

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Citation Number: 49

Abstract

Regiospecific, short, and efficient synthesis of the naturally occurring anthraquinones islandicin (la), digitopurpone lb), erythroglaucin (IC), catenarin (ld), cynodontin (le), and soranjidiol (If) have been achieved in 20-30% overall yields by using directed metalation of easily accessible methoxylated N, N-diethylbenzamides (3 and 10a--d) as the key step. In a representative example (Scheme IV), sequential treatment of N, N-di-ethyl-3, 5- ...