Total synthesis of Neocarzinostatin chromophore:
| Reference: | Hirama, M.; Gomibuchi, T.; Fujiwara, K.; Sugiura, Y.; Uesugi, M. J. Am. Chem. Soc. 1991, 113, 9851. DOI |
| Reactions: | O-H → O-SiEt3 • O-SiMe2tBu → O-H • CarboxAcid → CarboxEster • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • CompE+-Alkynyl-H/Vinyl-Br+M-R • Li-R → Sn-R • Li/H → Li-Alkynyl • Mg-Allenyl/Propargyl+Enone • Enone+Mg-R • Enone → Enone-α-Halo • Pd/Sn-Alkynyl+Vinyl-X • Cyclodecane • Propargyl-OH → Ynone • O-H → O-C(O)R • Li/H → Li-Alkynyl • Allyl-OH → Enone • |
| Reagents: | DMSO, (COCl)2 (Swern) • Br2 • Allenyl-MgX • BuLi(n), HMPA • SiEt3-Cl • BuLi(n) • SnBu3-Cl • DMSO, (COCl)2 (Swern) • Acetic acid • Carbodiimide • Pd(PPh3)4 • Carbonate, potassium • HMPA (solvent) • |