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Total synthesis of Peduncularine (partial):
| Reference: | Washburn, D. G.; Heidebrecht, R. W.; Martin, S. F. Org. Lett. 2003, 5, 3523. DOI |
| Reactions: | CarboxImide → Imine • Mg-R → Zn-R • Lactam enolate+Alkyl-X • Allyl-X+Enolate • Mg-Vinyl+Imine • Iminium+Mg-R • RCM → Ring-C • Cyclohexene • Bicyclo(321)-aza • Alkyl-X → Alkyl-SO2R • Imide → Aminal • |
| Reagents: | BH4-Na+ • HCl, EtOH • Sulfinic acid, benzene • Chloride, calcium • Vinyl-MgX • Vinyl-ZnX • LiNiPr2 • Allyl-Br • H2SO4 • Grubbs II • HOEt (react)} • |