Total synthesis of Jamtine (Simpkins):
| Reference: | Simpkins, N. S.; Gill, C. D. . Org. Lett. 2003, 5, 535. DOI |
| Reactions: | Lactam-5 • CarboxAmide → Imine • CompRed-CarboxImide/CarboxEster+M-H • Selenide → Selenoxide • Selenoxide-Ei → EneLactam • Lactam → EneLactam • Pictet-Spengler • Amine-6 • Lactam-5 • Bicyclo(430)-aza • Lactam → Lactam-α-SeR • N-C(O)R → N-CH2R • CompRed-CarboxAmide/CarboxEster+M-H • Asymmetric Deprotonation • Claisen acylation, Mander • CarboxAmide enolate+Acyl-X • Mander+enolate • Lactam → Lactam-α-SeR • |
| Reagents: | Acetic acid • BH4-Na+ • Sulfonic acid, Camphor • KH • H2O2 • Me3O+ X- • BH4-Na+ • Diselenide, phenyl • LiN(Phenethyl)R • Chiral base • Chiral base • O=C(OR)CN • |