Total synthesis of Amphidinolide-T1:
| Reference: | Colby, E. A.; O’Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2004, 126, 998-999 DOI |
| Reactions: | O-H → O-SiMe2tBu • Alkyl-OH → Aldehyde • Lactone-5 • O-SiMe2tBu → O-H • B-Allyl-Ipc+Aldehyde • Si-Allenyl+Aldehyde • Aldehyde+Si-R • Felkin-Anh • Ether-5 • CarboxAmide enolate(Evans)+Alkyl-X • Alkyl-X+Enolate • CarboxAmide enolate(Myers)+Alkyl-X • Alkyl-X+Enolate • Carbonickelation Alkyne • Alkyne+Epoxide • Carbonickelation Alkyne • Alkyne+Aldehyde • Lactone-9+ • Ozonolysis • CarboxAcid → CarboxEster • Takai-Lombardo → Ene • Ketone → C=CH2 • CompE+-Ketone/CarboxEster+M-R • Ether-5 • CarboxAmide(Evans) → Alkyl-OH • Hydroboration → Alkyl-OH • Lactone → Lactol • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • O-H → O-SiMe2tBu • Alkyl-OH → Alkyl-I • CarboxAmide → CarboxAcid • |
| Reagents: | LiNiPr2 • Propargyl-Br • AlH4-Li+ • SiMe2tBu-Cl • Epoxide • Ni(cod)2 • PBu3 • BEt3 • Crotyl-B(Ipc)2 • BH3·THF • H2O2, NaOH • RuO4-Pr4N+, NMO • AlHiBu2 • Allenyl-SiR3 • BF3·OEt2 • PPh3, I2 • LiNiPr2 • Hydroxide, sodium • Carbodiimide • Fluoride, R4N+ • Dess-Martin • Ni(cod)2 • PBu3 • BEt3 • SiMe2tBu-OTf • O3; Me2S • CH2I2, Zn°, ZrCl4 • PbCl2 • HF·Py • Chiral auxiliary (misc) • Imidazole • DMF (solvent) • |