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Regioselective N-Acylation of 3-Arylmethylpiperazine-2,5-diones: Short Synthesis of (-)-Glyantrypine and (-)-Fumiquinazoline F
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2001
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Combinatorial ChemistryEngineeringHeterocyclicShort SynthesisOrganic ChemistryStereoselective SynthesisChemistryRegioselective N-acylationFolded ConformationPharmacologyHeterocycle ChemistryFour-step Total SynthesisSynthetic ChemistryD-tryptophan Methyl EsterBiomolecular Engineering
The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from d-tryptophan methyl ester.