Download PDF
Synlett 2001; 2001(9): 1387-1390
DOI: 10.1055/s-2001-16785
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
28 August 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >