Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization

Toshiharu Noji; Hideto Fujiwara; Kentaro Okano; Hidetoshi Tokuyama

doi:10.1021/ol400597f

Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization

Toshiharu Noji, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama

PHA - Molecular Pharmaceutical Science

Tohoku University

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

47 Citations (Scopus)

Abstract

A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP) ₂·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.

Original language	English
Pages (from-to)	1946-1949
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1021/ol400597f
Publication status	Published - 2013 Apr 19

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10.1021/ol400597f

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abstract = "A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP) 2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.",

author = "Toshiharu Noji and Hideto Fujiwara and Kentaro Okano and Hidetoshi Tokuyama",

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AU - Noji, Toshiharu

AU - Fujiwara, Hideto

AU - Okano, Kentaro

AU - Tokuyama, Hidetoshi

PY - 2013/4/19

Y1 - 2013/4/19

N2 - A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP) 2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.

AB - A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP) 2·2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.

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VL - 15

SP - 1946

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Synthesis of substituted indoline and carbazole by benzyne-mediated cyclization-functionalization

Abstract

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