Total synthesis of Stenine:
| Reference: | Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aubé, J. J. Am. Chem. Soc. 2008, 130, 6018–6024. DOI |
| Reactions: | Ketone → EnolSilane • Li-Phosphonate+CarboxCl • ConjAdd M-N3 • Enone+Azide • HWE → Enone • Mechanism • N-C(O)R → N-CH2R • Diels-Alder, Enone • Bicyclo(440) • Schmidt reaction • Azide+Ketone • Amine-5 • Lactam-7 • Bicyclo(430)-aza • Bicyclo(540)-aza • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • CompE+-Lactone/Lactam+Base • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Lactone-5 • Ketone → Alkyl-OH • Lactone-5 • CompRed-Lactone/CarboxEster+M-H • CarboxAmide → Thioamide • CompE+-Lactam/Lactone+Lawesson • |
| Reagents: | P(O)(OR)2CH2-C(O)R' • Acrolein • NaH • SiMe3-OTf • Butadiene, 2-OR • SnCl4 • BH4-Na+ • LiN(SiMe3)2 • MeI • Lawesson • LiCH2-PO(OMe)2 • LiN(SiMe3)2 • Bromoacetate • |