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利用 Hg(OTf)2 催化的环化异构化反应全合成 (-)-Lepadiformine A。

Total Synthesis of (-)-Lepadiformine A Utilizing Hg(OTf)2-Catalyzed Cycloisomerization Reaction.

机构信息

Department of Chemistry, Graduate School of Science, Osaka City University , Sumiyoshi-ku, Osaka 558-8585, Japan.

出版信息

Org Lett. 2015 Dec 4;17(23):5772-5. doi: 10.1021/acs.orglett.5b02867. Epub 2015 Nov 19.

Abstract

A cytotoxic marine alkaloid (-)-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 (-)-lepadiformine A in 28% overall yield by featuring the novel Hg(OTf)(2)-catalyzed cycloisomerization.

摘要

一种细胞毒性海洋生物碱(-)-lepadiformine A(1)具有独特的结构,其特征在于反式 1-氮杂降蒈 AB 环系统与 AC 螺环系统融合。在这项研究中,我们发现氨基 ynone 2 到 1-氮杂螺[4.5]癸烷骨架 3 的环异构化反应(对应于 1 的 AC 环系统)由 Hg(OTf)(2)促进。因此,我们通过具有新颖的 Hg(OTf)(2)催化的环异构化反应,以 28%的总收率高效地完成了(-)-lepadiformine A 的全合成。

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