Skip to main content
. Author manuscript; available in PMC: 2016 Mar 24.
Published in final edited form as: Nat Prod Rep. 2015 Feb;32(2):328–347. doi: 10.1039/c4np00051j

Scheme 16.

Scheme 16

Reagents and conditions (a) Cl2CHOMe, TiCl4, CH2Cl2; (b) BBr3, CH2Cl2; (c) Br2, NaOAc, AcOH/CH2Cl2 (92%); (d) BrCH2Cl, Cs2CO3, MeCN, 110 °C (69%); (e) mCPBA, CHCl3, reflux; (f) 4 M HCl, MeOH/CH2Cl2, rt (73%, 2 steps); (g) R-Garner’s aldehyde (117) Ti(Oi-Pr)4, toluene, rt; (h) bromide, Cs2CO3, DMF, rt (65%, 2 steps); (i) TsOH·H2O, MeOH, rt; (j) 2,2-dimethoxypropane, TsOH·H2O, DMF, rt (84% 2 steps); (k) TBSOTf, 2,6-lutidine; MeOH; KF·2H2O, MeOH (76%); (l) ethyl glyoxalate, MS4A, toluene; (m) n-Bu3SnH, AIBN, benzene, reflux.