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Total synthesis of Pumiliotoxin B:
Reference: Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablock, J.. J. Am. Chem. Soc. 1996, 118, 9062. DOI
Keywords: CarboxAcid → Alkyl-OH • Alkyl-OH → Aldehyde • Alkene cleavage • Enone → Allyl-OH • O-SiPh2tBu → O-H • Diol-1,2 → Ketal • Li/I → Li-Vinyl • Corey-Fuchs • Wittig-ketomethyl → Enone • Fritsch-Buttenberg-Wiechell • CarboxAmide enolate(Evans)+Alkyl-X • Alkyl-X+Enolate • Al-Alkynyl+Epoxide • Epoxide+Al-R • Vinyl-I → Vinyl-H • Lemieux-Johnson oxidation • CarboxAmide(Evans) → CarboxAcid • Mannich carboiodination • Amine-6 •
Reagents: PPh3=C(Me)-C(O)R • Chiral auxiliary-Evans • LiN(SiMe3)2 • Allyl-I • H2O2, NaOH • AlH4-Li+ • DMSO, CF3CO2H (Moffat) • PPh3=CBr2 • OsO4, NaIO4 • AlHiBu2 • Fluoride, R4N+ • Me2C(OMe)2 • BuLi(n) • Epoxide • Hydroxide, barium • BuLi(tert) • Chloride, ammonium • AlEt2-Cl • Iodide, sodium • Formaldehyde • TsOH·Py •

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