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. Author manuscript; available in PMC: 2012 Jul 31.
Published in final edited form as: Chem Sci. 2010 Dec 24;2011(2):308–311. doi: 10.1039/C0SC00577K

Scheme 2.

Scheme 2

Construction of the second macrocyclic ring, dichloro installation and completion of the total synthesis of diazonamide A (1). Reagents and conditions: (a) AgTFA, NaHCO3, 2-amino-1-(4-bromo-1H-indol-3-yl)ethanone·TFA, DMF, 40 °C (b) PPh3, C2Cl6, NEt3, CH2Cl2, 0 °C (c) BBr3, CH2Cl2, −78 °C (d) PhNTf2, NEt3, CH2Cl2, rt (e) (Bpin)2, KF, 70 mol% Pd(PPh3)4, dioxane:H2O (20 : 1), MW 120 °C (f) NBS, THF; then LiOH, THF, MeOH, H2O (g) NCS, THF, 40 °C; then H2, Pd(OH)2, THF, 40 °C (h) TASF, DMF, rt.