Regioselective N-Acylation of 3-Arylmethylpiperazine-2,5-diones: Short Synthesis of (-)-Glyantrypine and (-)-Fumiquinazoline F

Fernando Hernández; Astrid Lumetzberger; Carmen Avendaño; Mónica Söllhuber

doi:10.1055/s-2001-16785

Synlett 2001; 2001(9): 1387-1390
DOI: 10.1055/s-2001-16785

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Regioselective N-Acylation of 3-Arylmethylpiperazine-2,5-diones: Short Synthesis of (-)-Glyantrypine and (-)-Fumiquinazoline F

Fernando Hernández^* , Astrid Lumetzberger, Carmen Avendaño, Mónica Söllhuber

^*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain; Fax 34-91-394 18 22; E-mail: msollhub@eucmax.sim.ucm.es

Abstract

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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.

regioselectivity - acylation - Wittig reactions - asymmetric synthesis - total synthesis

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