image

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
Keywords: Ketone → EnolSilane • Ketone → Alkyl-OH • Lactone-5 • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • CarboxAmide → Thioamide • CompE+-Lactam/Lactone+Lawesson • Li-Phosphonate+CarboxCl • ConjAdd M-N3 • HWE → Enone • Mechanism • CarboxAmide → Amine • Diels-Alder, Enone • Schmidt reaction • Azide+Ketone • Amine-5 • CompE+-Lactone/Lactam+LiNR2 • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Alkyl-X+Enolate •
Reagents: NaH • SiMe3-OTf • SnCl4 • BH4-Na+ • LiN(SiMe3)2 • MeI • Lawesson • LiN(SiMe3)2 • Bromoacetate •

Syntheses Home