Mal Dipakranjan, Roy Joyeeta
Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India.
Org Biomol Chem. 2015 Jun 14;13(22):6344-52. doi: 10.1039/c5ob00575b.
1-Hydroxycarbazole-2,3-dicarboxylates have been shown to undergo chemoselective reductive cyclization to furo[3,4-b]carbazolones on reaction with LiAlH4. One of the furocarbazolones is utilized to accomplish the first total synthesis of claulansine D and mafaicheenamine E in 9 and 6 steps respectively. The other key steps of the syntheses are addition of an allylic indium reagent and CC double bond isomerization.
1-羟基咔唑-2,3-二羧酸酯已被证明在与氢化铝锂反应时会发生化学选择性还原环化生成呋喃并[3,4-b]咔唑酮。其中一种呋喃并咔唑酮分别用于以9步和6步完成克劳兰辛D和马法奇烯胺E的首次全合成。合成的其他关键步骤是烯丙基铟试剂的加成和碳-碳双键异构化。
