Total synthesis of Epohelmin A:
| Reference: | Snider, B. B.; Gao, X. Org. Lett. 2005, 7, 4419-4422. DOI |
| Reactions: | O-Ethoxyethyl → O-H • Ketone enolate+Aldehyde • Aldol-Li → Aldol • Felkin-Anh • Reductive amination, H2 • Amine-5 • Bicyclo(430)-aza • HWE → Enone • Hydrogenation Imine • Imine → Amine • Li-Phosphonate+CarboxEster • Protecting group - CarboxAcid • O-H → O-Ethoxyethyl • Orthoester → CarboxEster • CarboxEster → CarboxEster • N-Cbz → N-H • |
| Reagents: | LiNiPr2 • Prolinal • Acetic acid • Carbonate, potassium • Vinyl-OR • H2, Pd • P(O)(OR)2CH2-C(O)R' • NaH • Acetic acid • TsOH·Py • HOMe (react) • |