Total synthesis of Phenserine (Overman):
| Reference: | Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043. DOI |
| Reactions: | Lactam enolate+Alkyl-X • Alkyl-X+Enolate • Reductive amination, Al-H • Amine-5 • Bicyclo(330)-aza • O-H → O-C(O)NR2 (phenol) • Ketal → Diol-1,2 • Diol-1,2 cleavage • O-Me → O-H (phenol) • |
| Reagents: | KN(SiMe3)2 • DMPU (solvent) • TsOH • Periodate, sodium • NH2Me • AlH4-Li+ • B(Br)3 • NaH • Isocyanate • |