Total synthesis of Strictamine:
| Reference: | Ren, W.; Wang, Q.; Zhu, J. Angew. Chem. Int. Ed. 2016, 55, 3500. DOI |
| Reactions: | Alkene → Diol-1,2 • Reductive amination, B-H • CompE+-Aldehyde/Ketone+amine • CompRed-Imine/Nitro+M-H • Ketone → Ketone-α-Halo • Ketone → Ketone-α-NR2 • Amine-6 • Bicyclo(331)-aza • Ammonium → Amine • N-Me → N-C(O)OR • Nitro → Amine • CompRed-Nitro/Ketone+M° • Pd-Carboxylation • EnolTriflate → EnoateEster • N-H → N-Allyl • CompNu-Amine/Imine+Alkyl-X • Ni-Heck coupling • Amine-6 • Bicyclo(331)-aza • Bicyclo(440)-aza • Diol-1,2 cleavage • Amine → Imine • Amine-5 • Bicyclo-(430)-aza • N-C(O)OR → N-H • |
| Reagents: | OsO4, NMO • Periodate, sodium • NHMe2 • BH(OAc)3-Na+ • TsOH • NBS • Iodide, sodium • DMSO (solvent) • Carbonate, potassium • O=C(OAllyl)Cl (Alloc) • Iodide, sodium • TiCl3 • Acetate, ammonium • Pd(PPh3)4 • CO • Allyl-Br • Vinyl-I • Carbonate, cesium • Ni(cod)2 • HSiEt3 • NEt3 • HOMe (react) • |