Synthetic studies of indoles and related compounds. XXVII. A new synthesis of crenatine from ethyl indole-2-carboxylate

DOI: 10.1248/cpb.39.2189

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 2189 - 2195 (1991)

Update date:2022-07-29

Topics:

Authors:

Murakami

Yokoyama

Aoki Aoki

Suzuki Suzuki

Sakurai Sakurai

Shinohara

Miyagi Miyagi

Kimura Kimura

Takahashi

Watanabe

Ohmoto Ohmoto

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.39.2189

Crenatine (1a), which is a member of a new class of β-carboline alkaloids having an oxygen functionality at the 4-position, was synthesized starting from ethyl 1-benzylindole-2-carboxylate (12a) via cyclization of an elaborated C₂-substituent to the 3-position of the indole nucleus and aluminum chloride-catalyzed debenzylation of the protected indolic nitrogen. 1-Ethyl-4-hydroxy-9-methyl-β-carboline (26b), a positional isomer of crenatine with regard to the methyl group, was also synthesized through the same methodology.

Full text of DOI:10.1248/cpb.39.2189

NII-Electronic Library Service

Products guided by the article

Product name:1-Propanone, 1-[1-(phenylmethyl)-1H-indol-2-yl]-

Cas No:112402-18-3

R&D Labs maybe for 112402-18-3

Yancheng Smiling Imp & Exp Co., Ltd.

Contact:+86-515-83173586

Address:Rm1207, BLD#03, Phoenix Plaza, Juheng Road, Yancheng, Jiangsu, P.R. China
Zhejiang Allied Chemical Co.,Ltd

Contact:18967038207

Address:Area A-30, High-tech Industrial Park, Quzhou, Zhejiang, China.
Chengdu Green technology Co.,Ltd.

Contact:86-28-82608355

Address:C9 ,Economic Headquarters, Economic Development Zone, Chengdu.
Hubei Danao Pharmaceutical Co.,Ltd.

website:http://www.danaopharm.com

Contact:+86-719-5251167

Address:Fandan Road,Danjiangkou,Hubei
Shangyu Sanhechemicals Co.,LTD.

Contact:86-0571-56696839

Address:Num.2952,Nanhuan Road,Binjiang District,Hangzhou,China

Relevant to this article

PtCl₂-catalyzed reactions of o-alkynylanilines with ethyl propiolate and dimethyl acetylenedicarboxylate

Doi:10.1016/j.tet.2008.11.095
(2009)
New synthesis of 1-[(3,4-dimethoxyphenyl)methoxymethyl]-6,7-dimethoxyisoquinoline (setigerine), a naturally occurring alkaloid, and some derivatives of papaverine

Doi:10.1016/j.tet.2008.11.077
(2009)
Live-cell imaging and profiling of c-Jun N-terminal kinases using covalent inhibitor-derived probes

Doi:10.1039/c8cc09558b
(2019)
Synthesis and estrogen receptor affinity of 2,3-diarylindoles

Doi:10.1002/ardp.19873200506
(1987)
Cyclization and ring-expansion processes involving samarium diiodide promoted reductive formation and subsequent oxidative ring opening of cyclopropanol derivatives

Doi:10.1021/jo802749g
(2009)
Photodesulfurization of indoline-2-thiones: A facile synthesis of indoles

Doi:10.1021/jo00241a042
(1988)

Article Doi