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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 2. Synthesis of Trichodermamide Aa.

Scheme 2

aReagents and conditions: a. KBH4, CeCl3, AcOH/THF (1:1), 0 °C; b. MeOC(O)Cl or EtOC(O)Cl, pyridine, PhMe/CH2Cl2 (2 : 1); c. Pd(PPh3)4 (10 mol %), N,O-bis(trimethylsilyl)acetamide (BTSA), PhMe; d. N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-ethylenediaminomanganese(III) chloride (23) (10 mol %), PhIO, cyclohexane/PhCF3 (1:1); e. PhSeH, NaHCO3, THF, 0 °C; f. TMSONa, CH2Cl2, 3 Å MS, then MsOH; g. 25a or 25b, HATU, sym-collidine, DMF; h. H2O2, pyridine, THF, 0 °C.