Total synthesis of Salinosporamide A:
| Reference: | Ma, G.; Nguyen, H.; Romo, D. Org. Lett. 2007, 9, 2143. DOI |
| Reactions: | N-H → N-PMB • Reductive amination, B-H • Zn-Allyl+Aldehyde • Aldehyde+Zn-R • Felkin-Anh • CompE+-Aldehyde/Lactone+M-R • Lactone-4 • Lactam-5 • Ketene Cycloaddition • Mechanism • Lactam-5 • N-H → N-C(O)R • CarboxEster → CarboxAcid (allyl) • Pd-Deallylation • O-Bn → O-H • CompRed-O-Bn/N-Bn+H2 • CarboxAcid → CarboxEster • Fischer esterification • Alkyl-OH → Aldehyde-α-NR2 • N-PMB → N-H • |
| Reagents: | Benzaldehyde • Allyl-OH • Ketene dimer • Pd(PPh3)4 • H2, Pd • DMSO, carbodiimide (Pfitzner–Moffatt) • Formic acid • Allyl-ZnX • Ceric ammonium nitrate • BH4-Na+ • NEtiPr2 • Pyridinium, 2-halo • DMAP • |