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Total synthesis of Eremantholide A New:
Reference: Boeckman, R. K.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682-9684. DOI
Keywords: Tebbe • Li/Br → Li-Vinyl • Ketone → EnolSilane • O-BOM → O-H • O-H → O-SO2R • Sulfide → Sulfone • Ketone → EnolEther • Aldehyde → Acetal • CarboxEster enolate+Alkyl-X • Cu-Vinyl+EnoateEster • EnoateEster+Cu-R • Aldol-Si • Alkyl-OH → Ketone-1,3-di • Ketone → EnolEther • Alkene cleavage • CompOx-Alkene/Enoate+OsO4 • Ketone → Alkyl-OH • CompRed-Ketone/Lactone+M-H • O-H → O-MOM • Claisen acylation, acyl-X • CarboxEster enolate+Acyl-X • KetoEster enolate+Alkyl-X • Enone → Enone-γ-Halo • Sulfone → α-Halosulfone • Ramberg-Baecklund •
Reagents: LiNiPr2 • Allyl-Br • AlMe3 • BuLi(tert) • HCl, H2O • Oxalic acid • SiMe3-Cl • DBU • BF3·OEt2 • Dess-Martin • HCl • OsO4, NaIO4 • BH4-Na+ • P2O5 • LiNiPr2 • NaH • MeI • SiMe3-Br • H2, Pd • TsCl, Py • LiNiPr2 • NBS • NaOMe • Sulfide, sodium • Oxone • NaH • KOtAm • HCl • HMPA (solvent) • HMPA (solvent) •

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