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Total synthesis of Stegobinone:
Reference: Matteson, D. S.; Man, H.-W.; Ho, O. C. J. Am. Chem. Soc. 1996, 118, 4560 DOI
Keywords: BoronateEster -> BoronicAcid • Alkyl-OH -> Ketone • Aldol-B • Alkyl-OH -> Ketone-1,3-di • Pyrone synthesis • B-Alkyl -> Alkyl-OH • Ley oxidation • Alkyl-OH -> Ketone • Li-Dichloromethyl+Borane • Li-Dichloromethyl+Borane • Mg-Alkyl+Borane • Metalate rearrangement (B) • O-Bn -> O-H • Metalate rearrangement (B) • Chiral auxiliary •
Reagents: LiCHCl2 • ZnCl2 • NaOBn • LiCHCl2 • MeMgCl • LiCHCl2 • H2O2 • Hydroxide, sodium • Cr2O7·2PyH (PDC) • BOTf-BBN • Cr2O7·2PyH (PDC) • H2O2 • MeSO3H • RuO4-Pr4N+ • MeMgCl • H2, Pd •

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