The synthesis of 2-methyltriclisine, an unnatural analog of the azafluoranthene alkaloid triclisine, is reported. The synthesis was achieved in 10 steps and 21 % overall yield from 2-bromo-3,4-dimethoxybenzaldehyde, through the intermediacy of 3,4-dimethoxyfluoren-9-one. Construction of the heterocyclic ring entailed the para-Claisen rearrangement of an allyl-4-fluorenyl ether, followed by isomerization of the resulting 2-allylfluoren-9-one and a microwave-assisted electrocyclization of the aza 6π-electron system formed by oximation of its carbonyl function. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)