Total synthesis of Crinine (Martin):
| Reference: | Martin, S. F.; Campbell, C. L. J. Org. Chem. 1988, 53, 3184 DOI |
| Reactions: | Aldol-enamine → Enone • Cyclohexenone • Pictet-Spengler • Amine-6 • Bicyclo(321) • Aldehyde azaenolate+Alkyl-X • Alkyl-X+Azaenolate • HWE → EnAmine • O-Allyl → O-H • Amine-5 • Pd-Deallylation • Ketone-α-Halo → Enone • N-Alloc → N-H • Pd-Deallylation • Enone → Allyl-OH • N-Bn → N-H • O-H → O-SO2Me • Allyl-X → Allyl-OAc • O-C(O)R → O-H • Ketal → Ketone • Ketone → Ketone-α-Halo • Alkyl-OH inversion • ConjAdd Amine • Bicyclo(430)-aza • |
| Reagents: | Pyrrolidine • Tribromide • DBU • Pd(PPh3)4 • AlH3 • Sulfonic anhydride, methane • NEt3 • Acetate, cesium • Carbonate, potassium • Formaldehyde • O=C(OR)Cl • HCl, H2O • P(O)(OR)2CH2-NR'2 • BuLi(n) • Bromoethylamine • |