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

Tomoki Itoh; Yuusuke Chiba; Shunsuke Kawaguchi; Yuki Koitaya; Yuuma Yoneta; Koji Yamada; Takumi Abe

doi:10.1039/c9ra02321f

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

Tomoki Itoh, Yuusuke Chiba, Shunsuke Kawaguchi, Yuki Koitaya, Yuuma Yoneta, Koji Yamada, Takumi Abe

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	10420-10424
Number of pages	5
Journal	RSC Advances
Volume	9
Issue number	18
DOIs	https://doi.org/10.1039/c9ra02321f
Publication status	Published - 2019
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

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10.1039/c9ra02321f

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abstract = "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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AU - Itoh, Tomoki

AU - Chiba, Yuusuke

AU - Kawaguchi, Shunsuke

AU - Koitaya, Yuki

AU - Yoneta, Yuuma

AU - Yamada, Koji

AU - Abe, Takumi

N1 - Funding Information: This work was nancially supported by JSPS (KAKENHI Grant Number 16K18849 for T. A.) as a Grant-in-Aid for Young Scientists (B). Publisher Copyright: © 2019 The Royal Society of Chemistry.

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

Abstract

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