Total synthesis of Biotin (Marquet):
| Reference: | Lavielle, S.; Bory, S.; Moreau, B.; Luche, M. J.; Marquet, A.J. Am. Chem. Soc., 1978, 100, 1558. DOI |
| Reactions: | Fischer esterification • CarboxAcid → CarboxEster • CarboxAcid → Alkyl-OH • Li-Sulfoxide+Alkyl-X • Alkyl-X+Li-R • CompE+-Alkyl-I/CarboxEster+M-R • Sulfoxide → Sulfide • CarboxEster → Alkyl-OH • CompRed-CarboxEster/Urea+M-H • N-H → N-Alkyl (2°) • Alkyl-X → Alkyl-SR • Sulfide-5 • N-H → N-C(O)NR2 • O-H → O-SO2Me • Sulfide → Sulfoxide • N-Bn → N-H • |
| Reagents: | NH2Bn • O=CCl2 • HOMe (react) • Sulfonyl chloride, methane • Sulfide, sodium • Periodate, sodium • LiCHR-Sulfinyl • Me-Li • TiCl3 • HBr • HMPA (solvent) • AlH4-Li+ • |