Total synthesis of Octalactin B:
| Reference: | O'Sullivan, P. T.; Buhr, W.; Fuhry, M. A. M.; Harrison, J. R.; Davies, J. E.; Feeder, N.; Marshall, D. R.; Burton, J. W.; Holmes, A. B.; J. Am. Chem. Soc. 2004, 126, 2194-2207. DOI |
| Reactions: | Allyl-OH → Enone • O-SiMe2tBu → O-H • Alkyne Hydrozirconation • Alkyne → Vinyl-I • B-Allenyl-Tartrate+Aldehyde • Aldehyde+B-Allenyl (asym) • Zr-Vinyl → X-Vinyl • O-H → O-SiMe2tBu • Li/H → Li-Alkynyl • Li-Alkynyl+Alkyl-X • Ketone → EnolBorane • Formylation EnolEther • Aldol-B-Ipc • Ketone enolate+Enal] (asym) • Enal+Enolate • Ketone → EnolBorane • Acetal → Aldehyde • Enol → EnolEster • Diol-1,3 → Carbonate • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Claisen-Ketene acetal • Petasis reagent • Carbonate → Ketene acetal • Hydrogenation alkene • Lactone-8 • Nozaki-Hiyama coupling • Cr-Vinyl+Aldehyde • Aldehyde+Cr-R • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • O-C(O)R → O-H (asym) • CompE+-Aldehyde/Lactone+M-R • |
| Reagents: | Dess-Martin • HF·Py • Chiral auxiliary (boronate) • Allenyl-BR2 • SiMe2tBu-Cl • BuLi(n) • ZrCp2ClH • I2 • Imidazole • MeI • Vinyl-OR • Orthoformate • BF3·OEt2 • Carbonate, sodium • HCl, H2O • Hydroxide, potassium • Acetic anhydride, NEt3 • B(Cl)(Ipc)2 • Chiral auxiliary (boronate) • Triphosgene • NEt3 • BH(OAc)3-Me4N+ • O=CCl2 • TiCp2Me2 (Petasis) • Al2O3 • HF·Py • Dess-Martin • Vinyl-I • CrCl2 • Lipase • NiCl2 • |