Concise Synthesis of the Bicyclic Scaffold of N-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization

A concise synthesis of the N-methylwelwitindolinone C isothiocyanate scaffold is disclosed. The approach relies on an indolyne cyclization to construct the [4.3.1]-bicyclic ring system present in the natural product. Subsequent oxidation of the indole core occurs with excellent diastereoselectivity...

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Veröffentlicht in:	Organic letters 2009-06, Vol.11 (11), p.2349-2351
Hauptverfasser:	Tian, Xia, Huters, Alexander D, Douglas, Colin J, Garg, Neil K
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Crystallography, X-Ray Cyclization Indole Alkaloids Indoles - chemical synthesis Indoles - chemistry Molecular Conformation Molecular Structure Oxidation-Reduction Stereoisomerism
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container_title	Organic letters
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creator	Tian, Xia Huters, Alexander D Douglas, Colin J Garg, Neil K
description	A concise synthesis of the N-methylwelwitindolinone C isothiocyanate scaffold is disclosed. The approach relies on an indolyne cyclization to construct the [4.3.1]-bicyclic ring system present in the natural product. Subsequent oxidation of the indole core occurs with excellent diastereoselectivity to afford oxindole 2, the structure of which was confirmed by X-ray crystallographic analysis.
doi_str_mv	10.1021/ol9007684
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subjects	Alkaloids - chemical synthesis Alkaloids - chemistry Crystallography, X-Ray Cyclization Indole Alkaloids Indoles - chemical synthesis Indoles - chemistry Molecular Conformation Molecular Structure Oxidation-Reduction Stereoisomerism
title	Concise Synthesis of the Bicyclic Scaffold of N-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization
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