Total synthesis of Sporidesmin A New:
| Reference: | Kishi, Y.; Nakatsuka, S.; Fukuyama, T.; Havel, M. J. Am. Chem. Soc. 1973, 95, 6493-6485. DOI |
| Reactions: | N-H → N-MOM • CarboxAmide → CarboxAmide-α-Br • CarboxAmide-α-Br → CarboxAmide-α-SR • Acetal(dithio) • Aryl-H → Aryl-Cl • N-H → N-Me • Indole synthesis • Friedel-Crafts Acylation • Decarbonylation • CarboxAmide enolate+Acyl-X • N-MOM → N-H • Ketone → Alkyl-OH • O-H → O-C(O)R • Oxyamination Alkene • O-C(O)R → O-H • Disulfide • |
| Reagents: | Chloromethyl ether • KOtBu • NBS • Benzoyl peroxide • HCl, MeOH • BF3·OEt2 • Cl2 • MeI • NaH • AlHiBu2 • Oxalyl chloride • BuLi(n) • HCl, H2O • AlHiBu2 • Acetic anhydride, Py • Iodosobenzene-OAc • Hydroxide, sodium • Perbenzoic acid, 3-chloro • |