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Total synthesis of Epothilone B, D (Part 1):
Reference: White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M.. J. Am. Chem. Soc. 2001, 123, 5407. DOI (Part 2)
Keywords: O-H → O-THP • O-H → O-SiMe2tBu • CarboxAmide(Evans) → CarboxEster(thio) • CarboxEster(thio)+Cu-R • Cu-Alkyl+CarboxEster(thio) • O-THP → O-H • Allyl-OH → Allyl-Br • Cu-Vinyl+EnoateAmide(Evans) • EnoateAmide(Evans)+Cu-R • ConjAdd Cu-R • Carbocupration Alkyne • Cu-Alkyl+Alkyne • HWE → Styrene • Wittig-methyl alkylation • Wittig-alkyl → Ene-cis • CompE+-Aldehyde/Ketone+Wittig • CarboxAmide enolate(Evans) Hydroxylation • Allyl-X → Allyl-Br • O-H → O-SO2R • Lemieux-Johnson oxidation • Alkene cleavage • Pinnick oxidation • Aldehyde → CarboxAcid • O-Bn → O-H • Alkyl-OH → Aldehyde • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • Ketone enolate+Aldehyde • Aldol-Li → Aldol • Felkin-Anh Chelation •
Reagents: CuI • DHP • Vinyl-Li • BuLi(tert) • Chiral auxiliary-Evans • Oxaziridine • NaN(SiMe3)2 • SiMe2tBu-OTf • Thiolate, ethyl • LiCuMe2 • P(O)(OR)2CH2-Ar • BuLi(n) • MgBr2 • Sulfonic anhydride, methane • PPh3=CH2 • PPh3=CH-Alkyl • LiN(SiMe3)2 • CuCN • I2 • Allyl-B(Ipc)2 • LiNiPr2 • SiMe2tBu-OTf • OsO4, NaIO4 • Chlorite, sodium • Diazomethane, silyl • H2, Pd • RuO4-Pr4N+, NMO • Chiral auxiliary-Boronate • SiMe2tBu-OTf • PPh3=CH-Alkyl •

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