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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
Keywords: Acetal → Aldehyde • Diol-1,3 → Carbonate • Ketone → Alkyl-OH • Carbonate → Ketene acetal • Claisen-Ketene acetal • Lactone-8 • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • Allyl-OH → Enone • O-SiMe2tBu → O-H • O-C(O)R → O-H • Petasis reagent • Carbonate → Ketene acetal • Formylation EnolEther • Aldol-B-Ipc • Ketone enolate+Enal • Enal+Enolate • Nozaki-Hiyama coupling • Cr-Vinyl+Aldehyde • Aldehyde+Cr-R • O-H → O-SiMe2tBu • Alkyne Hydrozirconation • Zr-Vinyl → X-Vinyl • Alkyne Hydrozirconation • Alkyne → Vinyl-I • B-Allenyl-Tartrate+Aldehyde • Hydrogenation alkene •
Reagents: Orthoformate • BF3·OEt2 • Carbonate, sodium • HCl, H2O • Hydroxide, potassium • Acetic anhydride, NEt3 • BCl(Ipc)2 • Triphosgene • NEt3 • BH(OAc)3-Me4N+ • TiCp2Me2 • Al2O3 • HF·Py • Dess-Martin • CrCl2 • Dess-Martin • HF·Py • Lipase • Chiral auxiliary-Boronate • Chiral auxiliary-Boronate • Allenyl-BR2 • SiMe2tBu-Cl • BuLi(n) • ZrCp2ClH • I2 • Imidazole • MeI •

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