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Total synthesis of Serricornin:
Reference: Matteson, D. S.; Singh, R. P. J. Org. Chem. 1998, 63, 4466. DOI
Keywords: B-Alkyl → HO-Alkyl • Alkene cleavage • Li-Dichloromethyl+Borane • Mg-Alkyl+Borane • Borane+Mg-R • Metalate rearrangement (B) • Lemieux-Johnson oxidation • B-Vinyl → H-Vinyl • Alkyne Haloboration • Li-Dichloromethyl+Borane • Li-Chloromethyl+Borane • Mg-Vinyl+Borane • Borane+Mg-R • Metalate rearrangement (B) •
Reagents: LiCHCl2 • MeMgCl • LiCHCl2 • EtMgX • H2O2, NaOH • B(Br)3 • Acetic acid • Mg° • OsO4, NaIO4 • LiCHCl2 • ZnCl2 • LiCH2-Cl • Vinyl-MgX • Chiral auxiliary-Boronate •

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