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Total synthesis of Stemoamide:
Reference: Torssell, S.; Wanngren, E. and Peter Somfai, P. J. Org. Chem. 2007, 72, 4246. DOI
Keywords: N-H → N-Alkyl • Seyferth-Gilbert homologation • Aldehyde → Alkyne • Haloboration Alkyne • CompRed-Alkyne/Alkene+B-H • Negishi coupling • Pd/Zn-Alkyl+Vinyl-X • RCM → Ring-C • Bromolactonization • Lactone-5 • Dehydrohalogenation → EneLactone • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • CompE+-Lactone/Lactam+LiNR2 • Hydrogenation EneLactone •
Reagents: NaN(SiMe3)2 • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • Diazophosphonate • Carbonate, potassium • B(I)-BBN • Acetic acid • Pd(PPh3)4 • Grubbs II • Hydroxide, lithium • Al2O3 • NEt3 • NiCl2 • BH4-Na+ • LiN(SiMe3)2

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