Total synthesis of Crinine (Muxfeldt) New:
| Reference: | Muxfeldt, H.; Schneider, R. S.; Mooberry, J, B. J. Am. Chem. Soc. 1966, 88, 3670–5671. DOI |
| Reactions: | Ketone → Ketone-α-NR2 • Nitroso synthesis • N=O → N-H • O-H → O-C(O)R • Robinson annulation, ketoester • KetoEster enolate+Enone • Cyclohexenone • CarboxEster → CarboxAcid • Decarboxylation β-keto acid • Enone → Allyl-OH • Claisen-Eschenmoser • N-C(O)R → N-H • Lactam-5 • Bicyclo(440)-aza • N-C(O)R → N-CH2R • Amine-5 • Pictet-Spengler • Amine-6 • Bicyclo(321) • Allylic oxidation → Enone • |
| Reagents: | Nitrite, sodium • Acetic acid • Acetic anhydride • Methyl vinyl ketone • Triton B • Hydroxide, sodium • BH4-Na+ • Hydroxide, sodium • AlH4-Li+ • Formaldehyde • SeO2 • Acetic anhydride • |