Issue 21, 2018, Issue in Progress

Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion

Abstract

The efficient formal total synthesis of histrionicotoxin alkaloids was achieved. In this process, two key reactions were used to construct a core 1-azaspiro[5.5]undecane framework common to histrionicotoxins: a mercuric triflate (Hg(OTf)2)-catalyzed cycloisomerization of a linear substrate, which was developed in our laboratory, and a samarium iodide (SmI2)-mediated ring expansion.

Graphical abstract: Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion

Supplementary files

Article information

Article type
Paper
Submitted
07 Mar 2018
Accepted
12 Mar 2018
First published
21 Mar 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 11296-11303

Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)2-catalyzed cycloisomerization and SmI2-induced ring expansion

K. Matsumura, K. Nishikawa, H. Yoshida, M. Doe and Y. Morimoto, RSC Adv., 2018, 8, 11296 DOI: 10.1039/C8RA02011F

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