Total synthesis of Eremantholide A:
| Reference: | Boeckman, R. K.; Yoon, S. K.; Heckendorn, D. K. J. Am. Chem. Soc. 1991, 113, 9682-9684. DOI |
| Reactions: | Tebbe • Li/Br → Li-Vinyl • O-Bn → O-H • Sulfide → Sulfone • Ketone → EnolEther • Aldehyde → Acetal • CarboxEster enolate+Alkyl-X • Allyl-X+Enolate • CarboxEster → ROC=CH2 • Cu-Vinyl+EnoateEster • EnoateEster+Cu-R • Mukaiyama Aldol • Aldol-Si • Aldehyde+EnolSilane • Alkyl-OH → Ketone-1,3-di • Ketone → EnolEther • Ether-5 • 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 • Cyclodecane • Alkyl-X → Alkyl-SR • O-H → O-SO2Ar • Ketone → EnolSilane • |
| Reagents: | LiNiPr2 • Allyl-Br • Vinyl-Br • Tebbe • BuLi(tert) • HCl, H2O • Oxalic acid • SiMe3-Cl • DBU • BF3·OEt2 • Dess-Martin • HCl, THF • OsO4, NaIO4 • BH4-Na+ • CH2(OMe)2 • P2O5 • LiNiPr2 • Acyl imidazole • NaH • MeI • SiMe3-Br • Amberlyst • H2, Pd • TsCl, Py • LiNiPr2 • NBS • NaOMe • Sulfide, sodium • Oxone • Amberlyst • NaH • Cl3C-CCl3 • KOtAm • HCl, H2O • HMPA (solvent) • HMPA (solvent) • |