Synthesis of Constrained Analogues of Tryptophan

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2015 Dec 15

PMID 26664620

Citations 1

Authors

Elisabetta Rossi

Valentina Pirovano

Marco Negrato

Giorgio Abbiati

Monica DellAcqua

Affiliations

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Abstract

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.

Citing Articles

Synthesis of Cyclohepta[]indoles by (4 + 3) Cycloaddition of 2-Vinylindoles or 4-Furo[3,2-]indoles with Oxyallyl Cations.

Pirovano V, Brambilla E, Moretti A, Rizzato S, Abbiati G, Nava D J Org Chem. 2020; 85(5):3265-3276.

PMID: 31975604 PMC: 7997566. DOI: 10.1021/acs.joc.9b03117.

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