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 |
| Reactions: | Acetal → Aldehyde • CarboxEster → Alkyl-OH • O-H → O-SO2Me • O-SiMe2tBu → O-H • O-H → O-SiMe3 • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Cycloaddition Ketene • Cyclobutane • Retro-Claisen • Li-Aryl+Aldehyde • Furan oxidation • Ether-6 • Mechanism • Ether-5 • Pd/Sn-Alkyl+Vinyl-X • Cr-Aryl+Aldehyde • Aldehyde+Cr-R • Nozaki-Hiyama coupling • Ether-9+ • Bicyclo(840) • Ketone-α-Halo → Ketone • O-H → O-SO2Me • Nitrile → Aldehyde • Li-Me+Ketone • Enone+Li-R • O-Piv → O-H • Ketone-α-OR → Ketone-1,2-di • Ketone → EnolTriflate • Alkyl-X → Alkyl-CN • Cyanide+Alkyl-X • O-H → O-Piv • Ketal → Ketal • CarboxAcid → CarboxEster • Ketal → Diol-1,2 • Li/Br → Li-Aryl • |
| Reagents: | Ketene • Zn° • Brederick reagent • TsOH • HOMe (react) • TsOH • Furyl-Li • AlHiBu2 • Sulfonyl chloride, methane • Cyanide, potassium • 18-crown-6 • AlHiBu2 • Piv-Cl • DMAP • Fluoride, R4N+ • Acetone (solvent) • Me-Li • 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 • SiMe2tBu-Cl • DMAP • Dioxirane • Alkynyl-SnR3 • HOMe (react) • |