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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 -> 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 • Alkyne -> Vinyl-I • B-Allenyl-Tartrate+Aldehyde • Hydrogenation Alkene •
Reagents: Orthoformate • BF3·OEt2 • Carbonate, sodium • HCl • 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 • Allenyl-BR2 • SiMe2tBu-Cl • BuLi(n) • ZrCp2ClH • I2 • Imidazole •

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