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Total synthesis of Pumiliotoxin B:
Reference: Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326. DOI
Keywords: CarboxAcid -> Alkyl-OH • Alkyl-OH -> Aldehyde • Alkene cleavage • Enone -> Allyl-OH • O-SiPh2tBu -> O-H • Diol -> Ketal • Li/I -> Li-Vinyl • Corey-Fuchs • Wittig-ketomethyl -> Enone • Fritsch-Buttenberg-Wiechell • CarboxAmide enolate(Evans)+Alkyl-X • Al-Alkynyl+Epoxide • Epoxide+Al-R • Vinyl-I -> Vinyl-H • Lemieux-Johnson oxidation • CarboxAmide(Evans) -> CarboxAcid • Mannich carboiodination • Amine-6 • Chiral auxiliary •
Reagents: PPh3=C(Me)-C(O)R • LiN(SiMe3)2 • Allyl-I • H2O2, NaOH • AlH4-Li+ • DMSO, CF3CO2H • PPh3=CBr2 • OsO4, NaIO4 • AlHiBu2 • Fluoride, Bu4N+ • Me2C(OMe)2 • BuLi(n) • Epoxide • Hydroxide, barium • BuLi(tert) • Chloride, ammonium • AlEt2-Cl • Iodide, sodium • Formaldehyde • TsOH·Py •

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