Total synthesis of Pumiliotoxin C (LeBel):
| Reference: | LeBel, N. A.; Balasubramanian, N J. Am. Chem. Soc. 1989, 111, 3363. DOI |
| Reactions: | Reductive amination, B-H • Li/H → Li-Sulfone • Ketone azaenolate+Alkyl-X • Alkyl-X+Azaenolate • Imine → Ketone • Ketone → Oxime • Nitrone synthesis • Aldehyde → Nitrone • Nitrone Cycloaddition • Amine-6 • Bicyclo(321)-aza • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Bicyclo(440)-aza • Alkyl-SO2R → Alkyl-H • N-OR → N-H • N-H → N-Boc • O-H → O-SO2Ar • Oxime → Hydroxylamine • N-Boc → N-H • |
| Reagents: | BuLi(n) • Allyl-Br • Periodate, sodium • NH2OH • BH3CN-Na+ • Zn° • Boc2O • TsCl, Py • BuLi(n) • HMPA (solvent) • Na(Hg) • Acetic acid, trifluoro • LiCHR-Sulfonyl • |