(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 a,5-piperazinedione and using
an aza-Wittig reaction for the preparation of the quinazoline system. The f
inal acid-promoted deprotection required tuning of the reaction conditions
in order to minimize a side reaction involving loss of the indolylmethyl si
de chain.