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Total synthesis of Biotin:
Reference: Fujisawa, T.; Nagai, M.; Koike, Y.; Shimizu, M. J. Org. Chem. 1994, 59, 5865. DOI
Keywords: N-Boc → N-H • N-H → N-C(O)NR2 • O-H → O-SO2R • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Hydrogenation EneSulfide • Felkin-Anh Chelation • N-H → N-Alkyl(2°) • Alkyne Hydrosulfidation • Sulfide-5 •
Reagents: Alkynyl-ZnX • TsOH • Isocyanate • KH • HMPA (solvent) • TsOH • Hydroxide, cesium • H2, Pd • HBr • Microbial oxidation •

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