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Paper | Regular issue | Vol 53, No. 8, 2000, pp.1765-1782
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8942
Synthesis of a Seco Analogue of Ardeemin

Esmeralda Caballero, Carmen Avendaño,* and J. Carlos Menéndez*

*Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain

Abstract

(1S,4S)-1-Indolylmethyl-4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazaline-3,6-dione, a seco analogue of ardeemin, was synthesized in six steps from L-tryptophan methyl ester via an N-protected 2,5-piperazinedione and using an aza-Wittig reaction for the preparation of the quinazoline system. The final acid-promoted deprotection required tuning of the reaction conditions in order to minimize a side reaction involving loss of the indolylmethyl side chain.