image

Total synthesis of Epothilone B, D:
Reference: White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M.. J. Am. Chem. Soc. 2001, 123, 5407. DOI
Keywords: O-H -> O-THP • O-H -> O-SiMe2tBu • CarboxAmide(Evans) -> CarboxEster(thio) • CarboxEster(thio) -> Ketone • O-THP -> O-H • Allyl-OH -> Allyl-Br • Lemieux-Johnson oxidation • Alkene cleavage • Pinnick oxidation • Aldehyde -> CarboxAcid • O-Bn -> O-H • Alkyl-OH -> Aldehyde • CarboxEster -> CarboxAcid • O-SiMe2tBu -> O-H • O-SiMe2tBu -> O-H • Diimide+Alkene • CompRed-Alkene/Alkene+Diimide • Cu-Vinyl+EnoateAmide(Evans) • EnoateAmide(Evans)+Cu-R • Carbocupration Alkyne • Cu-Alkyl+Alkyne • Alkyne+Cu-R • HWE -> Styrene • Wittig-methyl alkylation • Wittig-alkyl -> Ene-cis • CompE+-Aldehyde/Ketone+Wittig • Yamaguchi lactonization • Macrolactonization • Lactone-15+ • Epoxidation, dioxirane • CarboxAmide enolate(Evans) Hydroxylation • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Ketone enolate+Aldehyde • Aldol-Li -> Aldol • Allyl-OH -> Allyl-Br • Chiral auxiliary •
Reagents: CuI • DHP • Vinyl-Li • BuLi(tert) • Oxaziridine • NaN(SiMe3)2 • SiMe2tBu-OTf • Thiolate, ethyl • LiCuMe2 • P(O)(OR)2CH2-Ar • BuLi(n) • MgBr2 • MeSO2-O-SO2Me • PPh3=CH2 • PPh3=CH-Alkyl • Allyl-B(Ipc)2 • LiNiPr2 • SiMe2tBu-OTf • OsO4, NaIO4 • Chlorite, sodium • Diazomethane, silyl • H2, Pd • RuO4-Pr4N+, NMO • Hydroxide, sodium • Fluoride, Bu4N+ • Benzoyl chloride, 2,4,6-trichloro • Acetic acid, trifluoro • Acetic acid • Diimide • Dioxirane • SiMe2tBu-OTf • CuCN • I2

Syntheses Home