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. Author manuscript; available in PMC: 2014 Oct 25.
Published in final edited form as: J Nat Prod. 2013 Sep 20;76(10):10.1021/np400531b. doi: 10.1021/np400531b

Scheme 1.

Scheme 1

Synthesis of BCHP (5)

Reagents and Conditions a) n-BuMgCl, CuBr•DMS (20 mol%), −40 °C; then allylBr, Pd(PPh3)4 (10 mol%), 85%; b) OsO4 (3 mol%), NaIO4, EtOAc/H2O, 73%; c) NH4OAc, MeOH, reflux 98%; d) HCl, 14, then; NaOMe, MeOH, 80%.