Total synthesis of Cycloclavine (Wipf):
| Reference: | McCabe, S. R.; Wipf, P. Angew. Chem. Int. Ed. 2017, 56, 324-327 DOI See also: Racemic synthesis |
| Reactions: | EnolSilane → Ketone • Cyclopropanation Diazoester • Diazoester Cyclopropanation • Allene cyclopropanation • CarboxEster → Carboxamide • Enone → EnolSilane • Diels-Alder, Intram, Ene • Lactam-5 • Bicyclo(430)-aza • Spiro(52) • Ketone → Enone • Pd-Dehydrogenation • Li-Amine+Ketone • Ketone+Li-Alkyl • CompE+-Ketone/CarboxAmide+M-R • Furan cycloaddition • Diels-Alder, Intram, Ene • Indole synthesis • N-C(O)R → N-CH2R • N-C(O)OR → N-H • |
| Reagents: | Diazoacetate • DMAP • NaN(SiMe3)2 • SiMe2tBu-Cl • Butadiene, 2-OR • Microwave • Pd(OTFA)2 • O2 • Acetic acid • AlH4-Li+ • Fluoride, R4N+ • |