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Total synthesis of Biotin:
Reference: Confalone, P. N.; Lollar, E. D.; Pizzolato, G.; Uskokovic, M. R. J. Am. Chem. Soc., 1978, 100, 6291.DOI
Keywords: Nitro -> Nitrile oxide • Alkyl-X -> Alkyl-SR • N-H -> N-C(O)OR • Alkyl-OH -> Ketone • CarboxAmide -> CarboxAcid • Cycloaddition Nitrile oxide • Sulfide-5 • Beckman rearrangement • Allylic oxidation -> Allyl-Br • Wohl-Ziegler bromination • Oxime -> Amine • Thiolate+Vinyl-NO2 • ConjAdd M-SR • Urea •
Reagents: PhNCO • NEt3 • NBS • CS2 • NaOEt • AlH4-Li+ • O=C(OR)Cl • DMSO, Ac2O • NH2OH • Polyphosphoric acid • Hydroxide, barium • O=CCl2

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