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. Author manuscript; available in PMC: 2016 Dec 7.
Published in final edited form as: Org Biomol Chem. 2015 Sep 24;13(45):11078–11086. doi: 10.1039/c5ob01805f

Scheme 1.

Scheme 1

Synthesis of CP-1 and CP-2. ia) PPh3, DIAD, THF; 0 °C to r.t.; 16 h b) NaBH4, MeOH; 0 °C to r.t.; 3 h; 28% over 2 steps ii) K2CO3, Ac2O, DMF; 0 °C; 2 h; 58% iiia) 6-aminoquinoline, pyridine, triphosgene, DCM/toluene; 0 °C to reflux; 16 h b) TBAF, THF, acetic acid; r.t.; 15 h; 34% over 2 steps iv) HSO3Cl; r.t.; 15 h; 53% va) PPh3, THF/toluene b) H2SO4, MeOH; reflux; 2 days c) LiAlH4, THF; 0 °C to reflux; 15 h d) 1-chloro-2-octyne, KHCO3, DMF; r.t.; 15 h; 39% over 4 steps vi) K2CO3, Ac2O, DMF; 0 °C; 1 h; 79% viia) Na2CO3, triphosgene, toluene; 0 °C to r.t.; 4 h b) 6-aminoquinoline, THF; r.t.; 1 h; 26% over 2 steps. DIAD = diisopropyl azodicarboxylate; TBAF = tetrabutylammonium fluoride; TBDMS = tert-butyldimethylsilyl.