Total synthesis of Duocarmycin SA New:
| Reference: | Boger, D. L.; Machiya, K. J. Am. Chem. Soc. 1992, 112, 10056-10058. DOI |
| Reactions: | Resolution • Ketone enolate+Quinone • ConjAdd Enolate • Ketone enamine+Quinone • ConjAdd EnAmine • CarboxEster → Alkyl-OH • CompRed-CarboxEster/CarboxAmide+M-H • Diol-1,3 → Ketal • Quinone synthesis • Ketal → Diol-1,3 • Mitsunobu → Amine • Alkyl-OH → Alkyl-NR2 • Amine-5 • N-C(O)R → N-H • N-H → N-Boc • CompNu-N-H/N-H+RC(O)X • Acetal → Aldehyde • Aldehyde → CarboxEster • O-Bn → O-H (phenol) • Alkyl-OH → Alkyl-Cl • O-Boc → O-H • N-H → N-C(O)R • CompNu-N-H/N-H+RC(O)X • Cyclopropane • Indole synthesis • |
| Reagents: | Malonate • NaOMe • BH4-Na+ • Me2C(OMe)2 • TsOH • Pb(OAc)4 • HCl, MeOH • PPh3, DEAD • Hydrazine • Boc2O • Pd/C • Formate, ammonium • PPh3, CCl4 • MnO2 • Cyanide, sodium • HOMe (react) • HCl, H2O • Carbodiimide • NaH • DMF (solvent) • |