Total synthesis of Neocarzinostatin (Part 2):
| Reference: | Myers, A. G.; Glatthar, R.; Hammond, M.; Harrington, P. M.; Kuo, E. Y.; Liang, J.; Schaus, S. E.; Wu, Y.; Xiang, J.-N. J. Am. Chem. Soc. 2002, 124, 5380. DOI (Part 1) |
| Reactions: | O-SiMe2tBu → O-H • Ketal → Diol-1,2 • O-SiEt3 → O-H • Epoxide → Allyl-OH • CarboxAcid → CarboxEster • CompNu-O-H/O-H+RC(O)X • Dehydration → Enyne • Diol-1,2 → Carbonate • O-C(O)R → O-H • O-H → O-SiEt3 • CompNu-O-H/O-H+R3Si-X • O-H → O-C(O)R • |
| Reagents: | Chloroacetate • HF·NEt3 • Carbodiimide • TsOH • Sulfonic acid, Camphor • NH2Pr • SiEt3-OTf • Martin sulfurane • Epoxide • HF·NEt3 • PPh3, I2 • Imidazole • Chloroacetate • |