image

Total synthesis of Salinosporamide A:
Reference: Ma, G.; Nguyen, H.; Romo, D. Org. Lett. 2007, 9, 2143. DOI
Keywords: N-H → N-PMB • Fischer esterification • CarboxAcid → CarboxEster • O-Bn → O-H • Alkyl-OH → Aldehyde-α-NR2 • N-PMB → N-H • N-H → N-PMB • Reductive amination, B-H • N-H → N-Alkyl • Zn-Allyl+Aldehyde • Aldehyde+Zn-R • Felkin-Anh • CompE+-Aldehyde/Lactone+Zn-R • Lactone-4 • Lactam-5 • Ketene Cycloaddition • Mechanism • Lactam-5 •
Reagents: 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 •

Syntheses Home