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

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...

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Detalles Bibliográficos
Autores principales: Matsumura, Kunihiro, Nishikawa, Keisuke, Yoshida, Hiroaki, Doe, Matsumi, Morimoto, Yoshiki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079123/
https://www.ncbi.nlm.nih.gov/pubmed/35542821
http://dx.doi.org/10.1039/c8ra02011f
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author Matsumura, Kunihiro
Nishikawa, Keisuke
Yoshida, Hiroaki
Doe, Matsumi
Morimoto, Yoshiki
author_facet Matsumura, Kunihiro
Nishikawa, Keisuke
Yoshida, Hiroaki
Doe, Matsumi
Morimoto, Yoshiki
author_sort Matsumura, Kunihiro
collection PubMed
description 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 (SmI(2))-mediated ring expansion.
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spelling pubmed-90791232022-05-09 Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion Matsumura, Kunihiro Nishikawa, Keisuke Yoshida, Hiroaki Doe, Matsumi Morimoto, Yoshiki RSC Adv Chemistry 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 (SmI(2))-mediated ring expansion. The Royal Society of Chemistry 2018-03-21 /pmc/articles/PMC9079123/ /pubmed/35542821 http://dx.doi.org/10.1039/c8ra02011f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Matsumura, Kunihiro
Nishikawa, Keisuke
Yoshida, Hiroaki
Doe, Matsumi
Morimoto, Yoshiki
Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title_full Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title_fullStr Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title_full_unstemmed Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title_short Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion
title_sort formal total synthesis of histrionicotoxin alkaloids via hg(otf)(2)-catalyzed cycloisomerization and smi(2)-induced ring expansion
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9079123/
https://www.ncbi.nlm.nih.gov/pubmed/35542821
http://dx.doi.org/10.1039/c8ra02011f
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