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. Author manuscript; available in PMC: 2011 May 26.
Published in final edited form as: J Am Chem Soc. 2010 May 26;132(20):7119–7137. doi: 10.1021/ja1009458

Scheme 10.

Scheme 10

Initial route to psychotrimine precursor 107.a

aReagents and conditions: (a) 33 (3.0 equiv), CuI (0.30 equiv), (±)-trans-N,N′-dimethyl-1,2-cyclohexanediamine (0.60 equiv), K2CO3 (7.0 equiv), 1,4-dioxane, 101 °C, 20 h, 45%; (b) o-iodoaniline (1.2 equiv), N-iodosuccinimide (1.5 equiv), MeCN:MeOH 20:1, −45 °C, 1 h, 24%; (c) 103 (7 equiv), Pd(OAc)2 (0.3 equiv), K2CO3 (3.5 equiv), LiCl (1.0 equiv), DMF, 90 °C, 0.5 h, 70%.