Total synthesis of Stemoamide:
| Reference: | Torssell, S.; Wanngren, E. and Peter Somfai, P. J. Org. Chem. 2007, 72, 4246. DOI |
| Reactions: | CompE+-Carbamate/CarboxAmide+H2O • N-H → N-Alkyl • Seyferth-Gilbert homologation • Aldehyde → Alkyne • Haloboration Alkyne • Alkyne → Vinyl-I • Pd/Zn-Alkyl+Vinyl-X • RCM → Ring-N • Amine-7 • Bromolactonization • Lactone-5 • Dehydrohalogenation → EneLactone • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • CompE+-Lactone/Lactam+Base • Hydrogenation EneLactone • O-SiMe2tBu → O-H • Alkyl-OH → Aldehyde • B-Vinyl → H-Vinyl • |
| Reagents: | NaN(SiMe3)2 • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • Diazophosphonate • Carbonate, potassium • B(I)BBN • Acetic acid • Vinyl-I • Pd(PPh3)4 • Bromoacetate • Hydroxide, lithium • Al2O3 • NEt3 • BH4-Na+, NiCl2 • LiN(SiMe3)2 • Grubbs II • MeI • |