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

RSC Advances Pub Date: 2018-03-21 DOI: 10.1039/C8RA02011F

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
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