Total Synthesis of Epoxyeujindole A

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• 作者：Zhaohong Lu ; Hailong Li ; Ming Bian ; Ang Li
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：November 4, 2015
• 年：2015
• 卷：137
• 期：43
• 页码：13764-13767
• 全文大小：418K
• ISSN：1520-5126

文摘

The total synthesis of epoxyeujindole A, a structurally unusual indole diterpenoid isolated from Eupenicillium javanicum, has been accomplished for the first time. The synthesis features a late-stage cationic cyclization strategy, which took advantage of an electron-rich olefinic substrate. The CDE ring system was assembled via an enantioselective conjugate addition/alkylation, a Luche cyclization, and a Nozaki鈥揌iyama鈥揔ishi reaction. The heavily substituted A ring was constructed through a Suzuki鈥揗iyaura coupling and a cationic cyclization, and the bridged fused B ring was formed through a Prins reaction.