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Total synthesis of Pentenomycin I (Smith):
Reference: Branca, S. J,; Smith, A. B. J. Am. Chem. Soc. 1978, 100, 7767. DOI
Keywords: CarboxEster → Alkyl-OH • Ketal → Enone • O-SiMe2tBu → O-H • Enone → Enone-α-Halo • Ketone → Enone • Li-Vinyl+Aldehyde • Aldehyde+Li-Vinyl • O-H → O-SiMe2tBu • Ketal → Enone • Enone → Ketal • Ketone → Ketone-α-SeR • Selenoxide-Ei → KetoEsterEnone • KetoEster → Enone • Enone → Ketal • O-H → O-SiMe2tBu • Alkene → Diol-1,2 • Enone → Ketal • Li/Br → Li-Vinyl •
Reagents: Br2 • NEt3 • Glycol • Vinyl-Li • Glycol • AlHiBu2 • BuLi(n) • Formaldehyde • SiMe2tBu-Cl • OsO4 • SeO2 • Acetic acid • Imidazole • TsOH • NaH • SePh-Cl • H2O2

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