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. Author manuscript; available in PMC: 2011 Sep 3.
Published in final edited form as: J Org Chem. 2010 Sep 3;75(17):6019–6022. doi: 10.1021/jo101051w

Scheme 3. Synthesis of (+)-ipalbidinea.

Scheme 3

aReagents and conditions: (a) Pd(OAc)2 (30 mol%), Cu(OAc)2 (3 equiv), PMP–BF3K, K2CO3, t-BuOH/AcOH/DMSO (20:5:1), 60 °C; (b) L-Selectride, THF, −78 to 0 °C; (c) MeLi, THF, −78 °C; (d) SOCl2, pyridine, THF, −30 to −10 °C; (e) L-Selectride, THF, −78 to 0 °C; then Comins’ reagent, −78 to 0 °C; (f) Pd(PPh3)4 (10 mol%), MeZnBr, THF, 60 °C; (g) BBr3, CH2Cl2, −78 °C to rt. PMP = p-methoxyphenyl.