Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy

The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were co...

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Detalles Bibliográficos
Autores principales: Itoh, Tomoki, Chiba, Yuusuke, Kawaguchi, Shunsuke, Koitaya, Yuki, Yoneta, Yuuma, Yamada, Koji, Abe, Takumi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062488/
https://www.ncbi.nlm.nih.gov/pubmed/35520921
http://dx.doi.org/10.1039/c9ra02321f
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author Itoh, Tomoki
Chiba, Yuusuke
Kawaguchi, Shunsuke
Koitaya, Yuki
Yoneta, Yuuma
Yamada, Koji
Abe, Takumi
author_facet Itoh, Tomoki
Chiba, Yuusuke
Kawaguchi, Shunsuke
Koitaya, Yuki
Yoneta, Yuuma
Yamada, Koji
Abe, Takumi
author_sort Itoh, Tomoki
collection PubMed
description The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were constructed by a new Bischler–Napieralski-type cyclization, in which an unprecedented trichloromethyl carbamate serves as a reactive group.
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spelling pubmed-90624882022-05-04 Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy Itoh, Tomoki Chiba, Yuusuke Kawaguchi, Shunsuke Koitaya, Yuki Yoneta, Yuuma Yamada, Koji Abe, Takumi RSC Adv Chemistry The regioselective synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by two different cyclizations is described. The complete regioselectivity is controlled by the C4 Pictet–Spengler cyclization, in which an iminium ion acts as a transient directing (TDG) group. Furthermore, carbolines were constructed by a new Bischler–Napieralski-type cyclization, in which an unprecedented trichloromethyl carbamate serves as a reactive group. The Royal Society of Chemistry 2019-04-03 /pmc/articles/PMC9062488/ /pubmed/35520921 http://dx.doi.org/10.1039/c9ra02321f Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Itoh, Tomoki
Chiba, Yuusuke
Kawaguchi, Shunsuke
Koitaya, Yuki
Yoneta, Yuuma
Yamada, Koji
Abe, Takumi
Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title_full Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title_fullStr Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title_full_unstemmed Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title_short Total synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a double cyclization strategy
title_sort total synthesis of pyrano[3,2-e]indole alkaloid fontanesine b by a double cyclization strategy
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062488/
https://www.ncbi.nlm.nih.gov/pubmed/35520921
http://dx.doi.org/10.1039/c9ra02321f
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