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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 • Alkyl-OH → Ketone-1,3-di • Pyrone synthesis • B-Alkyl → HO-Alkyl • Alkyl-OH → Ketone • Li-Dichloromethyl+Borane • Li-Dichloromethyl+Borane • Mg-Alkyl+Borane • Borane+Mg-R • Metalate rearrangement (B) • O-Bn → O-H • Metalate rearrangement (B) • Aldol-B •
Reagents: LiCHCl2 • ZnCl2 • NaOBn • LiCHCl2 • MeMgCl • LiCHCl2 • H2O2 • Hydroxide, sodium • Cr2O7·2PyH (PDC) • B(OTf)-BBN • Cr2O7·2PyH (PDC) • H2O2 • Sulfonic acid, methane • RuO4-Pr4N+ • MeMgCl • H2, Pd • Chiral auxiliary-Boronate •

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