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. Author manuscript; available in PMC: 2016 Jul 1.
Published in final edited form as: J Am Chem Soc. 2015 Jun 22;137(25):8050–8053. doi: 10.1021/jacs.5b05205

Scheme 3. Synthesis of Trichodermamides B and Ca.

Scheme 3

aReagents and conditions: a. TMSONa, CH2Cl2, 3 Å MS, then MsOH, MeOH; b. 25a, HATU, sym-collidine, DMF; c. MeI, 18-crown-6, K2CO3, acetone, 40 °C; d. N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediaminomanganese(III) chloride (23) (10 mol %), PhIO, CH2Cl2; e. PhSeH, K2CO3, THF, 0 °C; f. H2O2, pyridine, THF, 0 °C; g. AcOOH, NaHCO3, CH2Cl2; h. Pd(PPh3)4 (10 mol %), PhSeH, PhMe; i. Li2CuBr4, THF; j. PhSeH, 1,8-bis(dimethylamino)naphthalene (Proton Sponge®, 30), THF, 0 °C; k. Ts2O, pyridine, 0 °C; l. H2O2, pyridine, THF, 0 °C; m. CaCl2, DMSO.