image

Total synthesis of Eleutherobin:
Reference: Chen, X.-T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E. Pettus, T. R. R.; Danishefsky, S. J. J. Am. Chem. Soc. J. . 1999, 121, 6563-657. DOI
Keywords: Ketone-α-Halo → Ketone • Acetal → Aldehyde • CarboxEster → Alkyl-OH • O-H → O-SO2R • Alkyl-OH → Alkyl-CN • Nitrile → Aldehyde • O-H → O-Piv • O-SiMe2tBu → O-H • Li-Me+Ketone • Enone+Li-R • O-H → O-SiMe3 • Ketal → Ketal • O-H → O-SiMe2tBu • O-C(O)R → O-H • Alkyl-OH → Ketone-α-OR • Ketone → EnolTriflate • O-SiMe2tBu → O-H • CarboxAcid → CarboxEster • Ketal → Diol-1,2 • Li/Br → Li-Aryl • Cycloaddition Ketene • Cyclobutane • Retro-Claisen • Li-Aryl+Aldehyde • Furan oxidation • Mechanism • Ether-5 • Pd/Sn-Alkyl+Vinyl-X • Stille coupling • Cr-Vinyl+Aldehyde • Aldehyde+Cr-R •
Reagents: Zn° • Bredereck reagent • TsOH • TsOH • Furyl-Li • AlHiBu2 • DMAP • Cyanide, potassium • 18-cr-6 • AlHiBu2 • Piv-Cl • DMAP • Fluoride, R4N+ • Dioxirane • MeLi • SiMe3-OTf • TsOH • SiMe2tBu-OTf • AlHiBu2 • RuO4-Pr4N+, NMO • LiN(SiMe3)2 • Pd(PPh3)4 • Chloride, lithium • Fluoride, R4N+ • Carbodiimide • TsOH·Py • BuLi(n) • CrCl2 • NiCl2

Syntheses Home