Total synthesis of Jamtine (Padwa):
| Reference: | Padwa, A.; Danca, M. D.; Hardcastle, K. I.; McClure, M. S. J. Org. Chem. 2003, 68, 929-941. DOI |
| Reactions: | Sulfide → Sulfoxide • Claisen acylation, formate • CarboxEster enolate+Formate • Sulfoxide-Ei → EneLactam • Lactam → EneLactam • CarboxAmide enolate+Alkyl-X • Alkyl-X+Enolate (intram) • Cyclohexane • Bicyclo(430)-aza • N-C(O)R → N-CH2R • Amine-5 • Aldehyde → EnAmine • CompRed-CarboxAmide/CarboxEster+M-H • Lactam-5 • Pummerer • Lactam-5 • Pictet-Spengler • Amine-6 • Bicyclo(430)-aza • N-H → N-C(O)R • Alkyl-OH → Alkyl-Br • Appel → Br • Sulfide → Sulfoxide • O-SiMe2tBu → O-H • CarboxAmide → Thioamide • |
| Reagents: | LiNiPr2 • Periodate, sodium • NaH • Periodate, sodium • Lawesson • Me3O+ X- • PPh3, CBr4 • Formate, ethyl • BH4-Na+ • Sulfonic acid, Camphor • |