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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 • Li-Allenyl/Propargyl+Alkyl-X • Alkyl-X+Li-R • Wittig-carboxymethyl → EnoateEster • Ketoester dianion+Alkyl-X • Alkyl-X+Enolate • Hydrogenation alkene • Alkyl-OH → Alkyl-H • Allyl-X → Allyl-Br • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Dehydration → Ene • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Allyl-X → Allyl-Br • O-H → O-SO2R • Finkelstein reaction • Lemieux-Johnson oxidation • KetoEster → Ester • Radical cyclization(α-Keto) •
Reagents: BuLi(n) • Allenyl-Li • Alkynyl-Li • Allyl-Cl • Formaldehyde • CuI • Sulfonyl chloride, methane, NEt3 • CH2=C(OLi)(OR) • AlH4-Li+ • Cr2O7·2PyH (PDC) • PPh3=C(Me)-CO2R • AlH4-Li+ • Sulfonyl chloride, methane • 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

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