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. Author manuscript; available in PMC: 2010 Mar 4.

Published in final edited form as: J Am Chem Soc. 2009 Mar 4;131(8):3069–3077. doi: 10.1021/ja8100566

Scheme 1 — 13-step synthesis of water-soluble triacetic acid cryptophane TAAC*

^*Conditions: (a) Cs₂CO₃, DMF, 55 °C, 12 h, 60%; (b) CHCl₃, HCOOH, reflux, 9 h, 40%; (c) Pd(OAc)₂, P(Ph)₃, (Et)₂NH, THF, H₂O, 80 °C, 4 h, 84%; (d) ethylbromoacetate, Cs₂CO₃, DMF, 60 °C, 12 h, 79%.; (e) KOH (2 M), THF, 70 °C, 12 h, 87%.