Synthesis of constrained analogues of tryptophan

Synthesis of constrained analogues of tryptophan

A Lewis acid-catalysed diastereoselective [4 + 2] cycloaddition of vinylindoles and methyl 2-acetamidoacrylate, leading to methyl 3-acetamido-1,2,3,4-tetrahydrocarbazole-3-carboxylate derivatives, is described. Treatment of the obtained cycloadducts under hydrolytic conditions results in the prepara...

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Main Authors: Elisabetta Rossi, Valentina Pirovano, Marco Negrato, Giorgio Abbiati, Monica Dell’Acqua
Format: Article
Language:English
Published: Beilstein-Institut 2015-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
constrained tryptophans
Diels–Alder
indoles
tetrahydrocarbazoles
unnatural amino acids
Online Access:https://doi.org/10.3762/bjoc.11.216
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spelling doaj-96180fb139e64b1b945945cd2c94b49b2021-02-02T06:59:30ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-10-011111997200610.3762/bjoc.11.2161860-5397-11-216Synthesis of constrained analogues of tryptophanElisabetta Rossi0Valentina Pirovano1Marco Negrato2Giorgio Abbiati3Monica Dell’Acqua4Dipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, ItalyDipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, ItalyDipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, ItalyDipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, ItalyDipartimento di Scienze Farmaceutiche, Sezione di Chimica Generale e Organica “A. Marchesini”, Università degli Studi di Milano, Via Venezian, 21, 20133 Milano, ItalyA Lewis acid-catalysed diastereoselective [4 + 2] cycloaddition of vinylindoles and methyl 2-acetamidoacrylate, leading to methyl 3-acetamido-1,2,3,4-tetrahydrocarbazole-3-carboxylate derivatives, is described. Treatment of the obtained cycloadducts under hydrolytic conditions results in the preparation of a small library of compounds bearing the free amino acid function at C-3 and pertaining to the class of constrained tryptophan analogues.https://doi.org/10.3762/bjoc.11.216constrained tryptophansDiels–Alderindolestetrahydrocarbazolesunnatural amino acids
collection DOAJ
language English
format Article
sources DOAJ
author Elisabetta Rossi
Valentina Pirovano
Marco Negrato
Giorgio Abbiati
Monica Dell’Acqua
spellingShingle Elisabetta Rossi
Valentina Pirovano
Marco Negrato
Giorgio Abbiati
Monica Dell’Acqua
Synthesis of constrained analogues of tryptophan
Beilstein Journal of Organic Chemistry
constrained tryptophans
Diels–Alder
indoles
tetrahydrocarbazoles
unnatural amino acids
author_facet Elisabetta Rossi
Valentina Pirovano
Marco Negrato
Giorgio Abbiati
Monica Dell’Acqua
author_sort Elisabetta Rossi
title Synthesis of constrained analogues of tryptophan
title_short Synthesis of constrained analogues of tryptophan
title_full Synthesis of constrained analogues of tryptophan
title_fullStr Synthesis of constrained analogues of tryptophan
title_full_unstemmed Synthesis of constrained analogues of tryptophan
title_sort synthesis of constrained analogues of tryptophan
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2015-10-01
description A Lewis acid-catalysed diastereoselective [4 + 2] cycloaddition of vinylindoles and methyl 2-acetamidoacrylate, leading to methyl 3-acetamido-1,2,3,4-tetrahydrocarbazole-3-carboxylate derivatives, is described. Treatment of the obtained cycloadducts under hydrolytic conditions results in the preparation of a small library of compounds bearing the free amino acid function at C-3 and pertaining to the class of constrained tryptophan analogues.
topic constrained tryptophans
Diels–Alder
indoles
tetrahydrocarbazoles
unnatural amino acids
url https://doi.org/10.3762/bjoc.11.216
work_keys_str_mv AT elisabettarossi synthesisofconstrainedanaloguesoftryptophan
AT valentinapirovano synthesisofconstrainedanaloguesoftryptophan
AT marconegrato synthesisofconstrainedanaloguesoftryptophan
AT giorgioabbiati synthesisofconstrainedanaloguesoftryptophan
AT monicadellacqua synthesisofconstrainedanaloguesoftryptophan
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