Total synthesis of Cephalotaxine (Mori):
| Reference: | Isono, N,; Mori, M. J. Org. Chem. 1995, 60, 115-119. DOI |
| Reactions: | Lactone enolate+Alkyl-X • Allyl-X+Enolate • Si-Vinyl → I-Vinyl • Aminal → Amine • N-H → N-Boc • CarboxAcid → CarboxEster • N-Boc → N-H • N-H → N-Alkyl • Friedel-Crafts Alkylation • Amine-7 • Bicyclo(530)-aza • Sn-Vinyl+Aldehyde • Aldehyde+Sn-R • Cyclopentene • Spiro(44)-aza • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde-α-NR2 • CompOx-Alkyl-OH/Amine+DMSO • Diol-1,2 → Ketone-1,2-di • Ketone → EnolEther • Diol-1,2 → Acetal • O-Me → O-H (phenol) • Enone → Allyl-OH • Alkene → Diol-1,2 • |
| Reagents: | LiNiPr2 • Vinyl-SiR3 • Allyl-Br • ICl • Fluoride, potassium • H2SO4 • Boc2O • Diazomethane • Acetic acid, trifluoro • DMSO (solvent) • Acetic acid, trifluoro • NEt3 • AlH4-Li+ • DMSO, Py·SO3 (Parikh-Doering) • Polyphosphoric acid • SnBu3-SiMe3 • Fluoride, cesium • B(Br)3 • CH2Br2 • NMe3(O) • DMSO, (CF3CO)2O • Orthoformate • BH4-Na+ • |