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.
Synthesis of constrained analogues of tryptophan / E. Rossi, V. Pirovano, M. Negrato, G. Abbiati, M. Dell’Acqua. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 11(2015 Oct 27), pp. 1997-2006. [10.3762/bjoc.11.216]
Synthesis of constrained analogues of tryptophan
E. RossiPrimo
;V. PirovanoSecondo
;G. AbbiatiPenultimo
;M. Dell’AcquaUltimo
2015
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.
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