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. Author manuscript; available in PMC: 2011 Apr 22.

Published in final edited form as: J Med Chem. 2010 Apr 22;53(8):3320–3329. doi: 10.1021/jm100047k

Scheme 3 — a. Synthesis of Acid Substituted Cyclofenil Analogs. Reagents: (a) TBDMSCl, imidazole, room temp, THF, 24 h; (b) i) Tf₂O, triethylamine, 0 °C to room temp, 8 h, ii) TBAF, rt, 15 min; (c) ethyl acrylate, Pd(PPh₃)₂Cl₂, triethylamine, DMF, 120 °C, 24 h; (d) ethyl 6-bromohexanoate, Cs₂CO₃, CH₃CN, room temp, 24 h; (e) BrCH₂COOCH₃, Cs₂CO₃, CH₃CN, room temp, 24 h; (f) 2 N KOH, MeOH, room temp, 24 h.

b. Synthesis of the Deoxy Analog (46) of Bicyclononane Compound 34 Reagents: (a) ethyl 6-bromohexanoate, Cs₂CO₃, CH₃CN, room temp, 24 h; (b) 2 N KOH, MeOH, room temp, 24 h.

Scheme 3 — a. Synthesis of Acid Substituted Cyclofenil Analogs. Reagents: (a) TBDMSCl, imidazole, room temp, THF, 24 h; (b) i) Tf₂O, triethylamine, 0 °C to room temp, 8 h, ii) TBAF, rt, 15 min; (c) ethyl acrylate, Pd(PPh₃)₂Cl₂, triethylamine, DMF, 120 °C, 24 h; (d) ethyl 6-bromohexanoate, Cs₂CO₃, CH₃CN, room temp, 24 h; (e) BrCH₂COOCH₃, Cs₂CO₃, CH₃CN, room temp, 24 h; (f) 2 N KOH, MeOH, room temp, 24 h.

b. Synthesis of the Deoxy Analog (46) of Bicyclononane Compound 34 Reagents: (a) ethyl 6-bromohexanoate, Cs₂CO₃, CH₃CN, room temp, 24 h; (b) 2 N KOH, MeOH, room temp, 24 h.