Total synthesis of Taxol (Part 1) New:
| Reference: | Fukaya, F.; Tanaka, Y.; Sato, A. C.; Kodama, K.; Yamazaki, H.; Ishimoto, T.; Nozaki, Y.; Iwaki, Y. M.; Yuki, Y.; Umei, K.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; Sato, T.; Chida, N. Org. Lett. 2015, 117, 2570-2573. DOI (Part 2) |
| Reactions: | O-H → O-SiMe2tBu • O-THP → O-H • CompE+-O-THP/O-MOM+H2O • Shapiro reaction • Cu-Vinyl+Enone • Enone+Cu-R • ConjAdd-Silylation • ConjAdd Cu-Vinyl • Mg-R → Cu-R • Mukaiyama Aldol • Aldol-Si • Aldehyde+EnolSilane • O-H → O-THP • Ketone → Alkyl-OH • O-H → O-MOM • Hydroboration → Alkyl-OH • Alkyl-OH → Aldehyde • Aldehyde+Li-Vinyl • Epoxidation, V • Epoxide reduction • Diol-1,2 → Carbonate • Allylic oxidation → Enone • O-H → O-C(O)R • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • Ketyl+Allyl-OR • Cyclooctane • Bicyclo(531) • Bicyclo(640) • Enone → Allyl-OH • |
| Reagents: | BuLi(n) • Vinyl-Li • Vinyl-MgX • CuI • TMEDA • SiMe3-Cl • NEt3 • Formaldehyde • Sc(OTf)3 • TsOH·Py • BH4-Na+, CeCl3 • Chloromethyl ether • BH2(Thexyl) • H2O2, NaOH • NEtiPr2 • SiMe2tBu-Cl • Imidazole • Acetic acid • RuO4-Pr4N+, NMO • Hydroperoxide, tbutyl - V • AlHiBu2 • O=CCl2 • Triphosgene • CrO3, DMP • BH(sBu3)-Li+ • Carbodiimide • DMAP • HF·Py • Acetonitrile (solvent) • Dess-Martin • SmI2 • HMPA (solvent) • |