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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: Alkyl-X → Alkyl-SR • N-H → N-C(O)OR • Alkyl-OH → Ketone • Ketone → Oxime • CarboxAmide → CarboxAcid • Beckman rearrangement • Allylic oxidation → Allyl-Br • Wohl-Ziegler bromination • Oxime → Amine • Thiolate+Vinyl-NO2 • ConjAdd M-SR • Urea • Nitro → Nitrile oxide • Cycloaddition Nitrile oxide • Sulfide-5 • CompOx-Alkyl-OH/Sulfide+DMSO •
Reagents: NBS • CS2 • NaOEt • AlH4-Li+ • O=C(OR)Cl • DMSO, Ac2O (Moffat) • NH2OH • Polyphosphoric acid • Hydroxide, barium • O=CCl2 • Isocyanate • NEt3

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