Total synthesis of Cermizine:
| Reference: | Shi,X,; Deng, Z.-T.; Zhu, Y.; Bao, Y.; Shao, L.-D.; Zhao, Q.-S. J. Org. Chem. 2017, 82, 11110. DOI |
| Reactions: | ConjAdd Cu-Alkyl • Cu-Benzyl+Enone • CarboxEster → CarboxEster • Michael Enal • CarboxEster enolate+Enal • Enal+Enolate • ConjAdd Enolate • O-Allyl → O-H • Pd-Deallylation • Decarboxylation β-keto acid • Reductive amination, B-H • Amine-6 • Bicyclo(440)-aza • N-H → N-SO2R • Hydrogenation Pyridine • Amine-6 • N-C(O)OR → N-CH3 • N-SO2R → N-H • |
| Reagents: | Benzyl-Li • CuI • DMAP • Acrolein • Fluoride, R4N+ • Pd(OAc)2 • PPh3 • BH4-Na+ • Acetate, ammonium • TsCl, NEt3 • H2, Pt • NEt3 • AlH4-Li+ • |