Total synthesis of Biotin (Confalone):
| Reference: | Confalone, P. N.; Lollar, E. D.; Pizzolato, G.; Uskokovic, M. R. J. Am. Chem. Soc., 1978, 100, 6291.DOI |
| Reactions: | Beckman rearrangement • Lactam-8 • Allylic oxidation → Allyl-Br • Wohl-Ziegler bromination • Oxime → Amine • Thiolate+EneNitro • ConjAdd M-SR • N-H → N-C(O)NR2 • Nitro → Nitrile oxide • Cycloaddition Nitrile oxide • Sulfide-5 • Alkyl-OH → Ketone • CompOx-Alkyl-OH/Sulfide+DMSO • Ketone → Oxime • Alkyl-X → Alkyl-SR • N-H → N-C(O)OR • CarboxAmide → CarboxAcid • |
| Reagents: | NBS • NEt3 • NaOEt • AlH4-Li+ • O=C(OMe)Cl • DMSO, Ac2O (Moffat) • NH2OH • Polyphosphoric acid • Hydroxide, barium • O=CCl2 • Isocyanate • NEt3 • |