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Synthesis of constrained analogues of tryptophan.

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.

SUBMITTER: Rossi E

PROVIDER: S-EPMC4661003 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Synthesis of constrained analogues of tryptophan.

Rossi Elisabetta E Pirovano Valentina V Negrato Marco M Abbiati Giorgio G Dell'Acqua Monica M

Beilstein journal of organic chemistry 20151027

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. ...[more]

PMID: 26664620

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