Total Synthesis of Bafilomycin A1 Kleinbeck, F.; Carreira, E.M., Angew. Chem. Int. Ed., 2008, 47, ASAP Me Ph O Me LDA, LiCl Me N OH Me Ph Br O O Me N OH Me MesO2S Bn Me Cy2BOTf, NEt3 O MesO2S OTES EtO I Me O Ph N Me Me Me 1) TESCl, DMAP, imidazole 2) DIBAL-H 3) TPAP, NMO, MS 4 Å 4) Ph3PC(Me)CO2Et A Me O I Me O OH O N Bn B I Me Me Me 1) DIBAL-H 2) TMSC CH, CuI, [Pd(PPh3)4], pyrrolidine 3) MnO2 O OTES H Me Me H Me Me D C 1) KHMDS, [18]crown-6, (iPrO)2P(O)CH(OMe)CO2Me 2) K2CO3 Me I Me Me H 2) DMP, py I Ph 1) LDA, BH3 NH3 E O OTES MeO OMe Me H Me Me TMS TMS 1) aq. LiOH 2) 2,4,6-trichlorobenzoylchloride, iPr2NEt 3) TASF OMe Me Me OH O TEMPO, PhI(OAc)2 Me OH OH O Me Me Me OMe Me I OMe Me Me OH O O 1) TMSCl, NEt3, LiHMDS 2) 1, BF3 OEt, MS 4 Å 3) TASF TBSO Me Me iPr Me Me OH O Me OMe Me OMe Me O HO H iPr O HO OH O Me OH O Me Me OMe Me J 1 Me Bafilomycin A1 Me TBDPSO OH N Me OTr H Me Me O O Me N O Me OTr Me 1) Me4NBH(OAc)3 2) TsOH, 2,2-dimethoxypropane 3) aq. LiOH 4) NaIO4 on silica gel OH Me Me TBDPSO OH F TBDPSO tBuOCl; then F, iPrOH, EtMgBr Me OH Me Me TBDPSO O G TBDPSO O O OH OMe Me OTES Me Me OMe Me Me O Me 1) (EtO)3SiH, [Cp*Ru(CNMe)3]PF6 2) TBAF, CuI 3) MeI, NaH Me Me Me MeO2C O OTES Me Me Me Me MeO2C Me Me E, Zn(OTf)2, (+)-NME, iPr2NEt O O H Me OMe Me TBDPSO O Me O OMe Me 1) TsOH H2O 2) triphosgene, py 3) Raney-Ni, B(OH)3, H2 Me OH 1) HF py 2) AcO(O)CH, DMAP 3) CSA; K2CO3 TBDPSO MeO2C OH OH Me Me Me H Me Me OMe Me
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