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Total synthesis of Upial:
Reference: Taschner, M. J.; Shahripour, A. J. Am. Chem. Soc. 1985, 107, 5570. DOI
Keywords: Wittig-methoxymethyl • Reductive formylation • Alkene cleavage • Haloform • Lactone-5 • Bredt's Rule • ConjReduct-Alkylation • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Enone ConjReduct • Alkyl-X+Enolate • Lactone enolate+Alkyl-X • Lactone-5 • Alkyl-X+Enolate • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Aldol-H+ → Aldol • Cyclohexanone • Dehydration → Ene • Alkene cleavage • Lemieux-Johnson oxidation • CompE+-Aldehyde/Ketone+Wittig • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Lactone-5 • CarboxEster → CarboxAcid • Lactone-5 • CarboxEster → Alkyl-OH • Alkyl-OH → Aldehyde • Alkyl-OH → Ketone •
Reagents: Li°/NH3 • Bromoacetate • Hydroxide, potassium • Li°/NH3 • LiNiPr2 • AlH4-Li+ • DMSO, (COCl)2 (Swern) • NEt3 • PPh3=CH-OMe • HCl, H2O • MeMgBr • OsO4, NaIO4 • SOCl2 • BH3CN-Na+ • Acetic acid • LiNiPr2, HMPA • Allyl-Br • OsO4, NaIO4 • Hypochlorite, potassium • DMSO, (COCl)2 (Swern) • MeI • HMPA (solvent) •

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