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

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