Total synthesis of Dynemycin A, tetra-O-Me New:
| Reference: | Taunton, J.; Wood, J. L.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10378-10379. DOI. (Synthesis of starting material) |
| Reactions: | Friedel-Crafts Alkylation • Benzyl-OR → Benzyl-H • CarboxAcid → CarboxCl • Friedel-Crafts Acylation • Benzylic oxidation → Benzyl-OR • Epoxidation, peracid • N-C(O)OR → N-H • Hydroquinone → Quinone • Quinone synthesis • O-H → O-Me (phenol) • |
| Reagents: | AgOC(O)CF3 • Sulfate, dimethyl • HSiEt3 • AlMeCl2 • SOCl2 • SiMe3-OTf • DDQ • Perbenzoic acid, 3-chloro • DBU • Ceric ammonium nitrate • Acetonitrile (solvent) • MeI • |