Total synthesis of Taxol (Part 2) New:
| Reference: | Fukaya, F.; Kodama, K.; Tanaka, Y.; Yamazaki, H.; Sugai, T.; Yamaguchi, Y.; Watanabe, A.; Oishi, T.; Sato, T.; Chida, N. Org. Lett. 2015, 117, 2574-2577. DOI (Part 1) |
| Reactions: | Alkyl-OH → Ketone • Ketone → Alkyl-OH • O-H → O-Bn • Alkene → Diol-1,2 • O-H → O-C(S)SR • Xanthate pyrolysis • O-MOM → O-H • Alkyl-OH → Ketone • Mg-Silane • CompE+-Ketone/CarboxEster+M-R • Mg-R → Zn-R • Hydrogenation Diene • Allyl-OH → Enone • Peterson → Ene • O-C(O)R → O-H • Diol-1,2 → Carbonate • CompNu-O-H/O-H+RC(O)X • O-H → O-SiEt3 • Allylic oxidation → Allyl-OH • O-H → O-SO2Me • Alkene → Diol-1,2 • Williamson etherification • Ether-4 • Bicyclo(430)-oxa • O-H → O-Alkyl • |
| Reagents: | RuO4-Pr4N+, NMO • BH4-Na+ • Benzyl-X • NaH • OsO4 • CS2 • NaH • MeI • TsOH·Py • RuO4-Pr4N+, NMO • H2, Pd • RuO4-Pr4N+, NMO • BF3·OEt2 • Carbonate, potassium • O=CCl2 • Triphosgene • SiEt3-OTf • SeO2 • Hydroperoxide, tbutyl • Sulfonyl chloride, methane, Py • OsO4 • NEtiPr2 • HMPA (solvent) • ZnCl2 • |