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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.

SUBMITTER: Matsumura K

PROVIDER: S-EPMC9079123 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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

Matsumura Kunihiro K Nishikawa Keisuke K Yoshida Hiroaki H Doe Matsumi M Morimoto Yoshiki Y

RSC advances 20180321 21

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. ...[more]

PMID: 35542821

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