Total synthesis of Tubingensin A (Garg):
| Reference: | Goetz, A. E.; Silberstein, A. L.; Corsello, M. A. Garg, N. K. J. Am. Chem. Soc. 2014, 136, 3036-3039. DOI |
| Reactions: | Aryl-H → Aryl-Br • Carbazole synthesis • O-H → O-Tf (phenol) • N-H → N-MOM • ConjAdd-Silylation • Cu-Vinyl+Enone • Mg-R → Cu-R • ConjAdd-Silylation • Cu-Allyl+Enone • Enone+Cu-R • Hydroboration → Alkyl-B • CompRed-Alkene/Alkene+M-H • Pd/B-Alkyl+Aryl-X • EnolSilane+Iminium • Mannich • Iminium+Enolate • Benzyne addition • Bicyclo(440) • Amine → AmineOxide • N-MOM → N-H • Ketone → Alkyl-OH • Cope elimination • |
| Reagents: | NBS • Tf2O • NEt3 • Chloromethyl ether • NaH • Vinyl-MgX • CuI • HMPA (solvent) • BH-BBN • Alkyl-BR2 • Pd(PPh3)4 • DMF (solvent) • CH2=NMe2+I- • Allyl-Li • CuCN • SiEt3-Cl • NaNH2 • HCl, H2O • Alkyl-BR2 • Perbenzoic acid, 3-chloro • |