Total Synthesis of (鈭?-Lepadiformine A Utilizing Hg(OTf)2-Catalyzed Cycloisomerization Reaction
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- 作者：Keisuke Nishikawa ; Seiho Kikuchi ; Shinnosuke Ezaki ; Tomoyuki Koyama ; Haruka Nokubo ; Takeshi Kodama ; Yoshimitsu Tachi ; Yoshiki Morimoto
- 刊名：Organic Letters
- 出版年：2015
- 出版时间：December 4, 2015
- 年：2015
- 卷：17
- 期：23
- 页码：5772-5775
- 全文大小：385K
- ISSN：1523-7052
文摘
A cytotoxic marine alkaloid (鈭?-lepadiformine A (1) possesses a unique structure characterized by the trans-1-azadecalin AB ring system fused with the AC spiro-cyclic ring. In this research, we found that a cycloisomerization reaction from amino ynone 2 to a 1-azaspiro[4.5]decane skeleton 3, corresponding to the AC ring system of 1, is promoted by Hg(OTf)2. Thus, we have accomplished the efficient total synthesis of (鈭?-lepadiformine A in 28% overall yield by featuring the novel Hg(OTf)2-catalyzed cycloisomerization.