Synthesis of a seco analogue of ardeemin

Abstract

(1S,4S)-1-Indolylmethyl-4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]-q uinazaline-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.