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Total synthesis of Biotin:
Reference: Lavielle, S.; Bory, S.; Moreau, B.; Luche, M. J.; Marquet, A.J. Am. Chem. Soc., 1978, 100, 1558. DOI
Keywords: Fischer esterification • CarboxAcid → CarboxEster • CarboxAcid → Alkyl-OH • Sulfide → Sulfoxide • N-Bn → N-H • Li-Sulfoxide+Alkyl-X • Alkyl-X+Li-R • CompE+-Alkyl-I/CarboxEster+Li-R • Sulfoxide → Sulfide • CompE+-CarboxEster/Urea+LiAlH4 • N-H → N-Alkyl(2°) • Alkyl-X → Alkyl-SR • Sulfide-5 • Urea • CarboxEster → Alkyl-OH •
Reagents: NH2Bn • O=CCl2 • Sulfonyl chloride, methane • Sulfide, sodium • Periodate, sodium • LiCHR-Sulfinyl • MeLi • TiCl3 • HBr • HMPA (solvent) • AlH4-Li+

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