image

Total synthesis of Isosteviol:
Reference: Snider, B. B.; Keselgof, J. Y.; Foxman, B. M. J. Org. Chem. 1998, 63, 7945. DOI
Keywords: O-H -> O-SO2R • CarboxEster -> Alkyl-OH • Alkyl-OH -> Aldehyde • CarboxEster -> Alkyl-OH • Ketone -> Alkyl-OH • Alkene cleavage • CarboxEster -> Alkyl-OH • Jones oxidation • Alkyl-OH -> CarboxAcid • Carbocupration Alkyne • Cu-Allyl+Alkyne • CarboxEster enolate+Alkyl-X • Li-Allenyl/Propargyl+Alkyl-X • Wittig-carboxymethyl -> EnoateEster • Ketoester dianion+Alkyl-X • Hydrogenation Alkene • Alkyl-OH -> Alkyl-H • Allyl-OH -> Allyl-Br • CarboxEster enolate+Alkyl-X • Dehydration -> Ene • Li-Alkynyl+Aldehyde • Li/H -> Li-Alkynyl • Allyl-OH -> Allyl-Br • Finkelstein reaction • Lemieux-Johnson oxidation • KetoEster -> Ester • Radical cyclization(α-Keto) •
Reagents: BuLi(n) • Allenyl-Li • Alkynyl-Li • Allyl-Cl • Formaldehyde • CuI • MeSO2Cl, NEt3 • CH2=C(OLi)(OR) • AlH4-Li+ • Cr2O7·2PyH (PDC) • PPh3=C(Me)-CO2R • AlH4-Li+ • MeSO2Cl • Acetoacetate • NaH • BH4-Na+ • OsO4, NaIO4 • PPh3, DEAD • H2, Pt • AlH4-Li+ • CrO3, H2SO4 (Jones) • Allyl-MgX • CuI • BuLi(n) • Bromide, lithium • HMPA (solvent) • Mn(OAc)3 • Cu(OAc)2

Syntheses Home