Total synthesis of Vineomycinone B2, Methyl Ester (Tius):
| Reference: | Tius, M. A.; Gu, X. Q.; Gomez-Galeno, J. J. Am. Chem. Soc. 1990, 112, 8188–8189. DOI |
| Reactions: | O-SiMe2tBu → O-H • O-MOM → O-H • Pd/Zn-Vinyl+Aryl-X • Li/H → Li-Vinyl-OR • Li-R → Zn-R • Hydrogenation EnolEther • Li/H → Li-Aryl • Pd/Sn-Aryl+Allyl-X • Cu-Me+EnoateEster • Anthraquinone synthesis • Li-R → Sn-R • CarboxAcid → CarboxEster • |
| Reagents: | BuLi(tert) • ZnCl2 • PPh3 • BH3CN-Na+ • HCl, MeOH • BuLi(n) • SnBu3-Cl • Pd2(dba)3 • Me-Cuprate • Permanganate, silver • HCl, MeOH • Aryl-Li • HOMe (react) • |