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. Author manuscript; available in PMC: 2008 Aug 28.

Published in final edited form as: J Org Chem. 2005 Aug 5;70(16):6496–6498. doi: 10.1021/jo050831t

SCHEME 3 — Synthesis of Indenoisoquinoline 4 from trans-3^a

^aReagents and conditions: (a) TMSCHN₂, MeOH-benzene (2:7), room temperature, 30 min (99%); (b) (1) NaHMDS, PhSeCl, –78 ºC to room temperature, 12 h, (2) H₂O₂, AcOH, room temperature, 12 h (85%); (c) LiOH•H₂O, THF-MeOH-H₂O, reflux, 36 h (91%); (d) SOCl₂, room temperature, 12 h (84%).