Total synthesis of Cephalotaxine (Mariano):
| Reference: | Lin, X.; Kavash, R. W.; Mariano, P. S. J. Org. Chem.. 1996, 61, 7335-7347. DOI |
| Reactions: | Li/I → Li-Aryl • Acetal → Aldehyde • N-Bn → N-H • Li-Aryl+CarboxAmide • CarboxAmide+Li-R • Mukaiyama Aldol • Aldol-Si • Aldehyde+EnolSilane • Pinacol • Cyclopentenone • Ether-7 • Enone-β-OR+Mg-R • Mg-Alkyl+Ketone • Enone-β-OR → Enone • Stork-Danheiser • Reductive amination, B-H • CompE+-Aldehyde/Ketone+amine • N-H → N-Alkyl • Ketone → Ketone-α-OR • Oxaziridine+Enolate • Alkyl-OH → Ketone-1,2-di • CompOx-Alkyl-OH/Amine+DMSO • ConjAdd Amine • Ketone → EnolEther • Amine-5 • Amine-9+ • N-H → N-Boc • O-H → O-SO2Me • N-Boc → N-H • Enone → Allyl-OH • |
| Reagents: | BuLi(n) • DMF (react) • BF3·OEt2 • Alkyl-MgX • Sulfonyl chloride, methane, NEt3 • HCl, H2O • NH2Bn • BH3CN-Na+ • NEtiPr2 • H2, Pd • Oxaziridine • LiNiPr2 • DMSO, (CF3CO)2O • Me2C(OMe)2 • BH4-Na+ • |