Total synthesis of Fastigiatine:
| Reference: | Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594–9595. DOI |
| Reactions: | N-Boc → N-H • CarboxAcid → CarboxEster • Williamson esterification • N-H → N-Boc • Cyclopropane alkylation • Cu-Vinyl+Cyclopropane • CarboxEster enolate+Alkyl-X • Alkyl-X+Enolate • Alkyl-X → Alkyl-N3 • CarboxEster → CarboxAcid • Decarboxylation malonic • N-H → N-SO2R • CarboxEster enolate+CarboxAmide • Claisen acylation, acyl-X • Staudinger • Aza-Wittig • Aldol-enamine → Aldol • Bicyclo(440)-aza • Bicyclo(331) • Spiro(54) • N-SO2R → N-H • N-H → N-Me • Amine-5 • Decarboxylation β-keto acid • N-H → N-C(O)R • ConjAdd EnAmine • Enone+EnAmine • Amine-6 • |
| Reagents: | KH • Boc2O • Carbonate, cesium • Azide, sodium • Fluoride, R4N+ • DBU • Mg(ClO4)2 • LiN(SiMe3)2 • CH2=C(OLi)(OR) • LiNiPr2 • PPh3 • Carbonate, potassium • MeI • CF3CH2OH (solvent) • TsOH • Acetic anhydride, NEt3 • |