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Total synthesis of Nakienone B:
Reference: Pour, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 4679. DOI
Keywords: O-H -> O-SiMe2tBu • Luche reduction • Enone -> Allyl-OH • O-H -> O-SiMe3 • O-H -> O-SiMe2tBu • Li-Vinyl -> Zn-Vinyl • Allyl-OH -> Enal • Allyl-OH -> Enone • O-SiMe2tBu -> O-H • Birch reduction • Wittig-methyl -> Diene • Li/I -> Li-Vinyl • Alkyne Hydroalumination • Li-Alkynyl+Aldehyde • Li/H -> Li-Alkynyl • Enone -> Enone-α-Halo • Epoxide -> Allyl-OH • Epoxidation, peracid • CompE+-Vinyl-I/RO-SiMe3+Li-R • Pd/Zn-Vinyl+Vinyl-X • Negishi coupling •
Reagents: Li°/NH3 • Al2O3 • SiMe2tBu-Cl • I2, Py • BH4-Na+, CeCl3 • SiMe3-Cl • SiMe2tBu-Cl • Alkynyl-Li • Formaldehyde • AlH4-Li+ • I2 • BuLi(n) • ZnBr2 • DMSO, (COCl)2 • PPh3=CH2 • DMSO, (COCl)2 • Fluoride, Bu4N+ • Vinyl-ZnX • Pd(PPh3)4 • Carbonate, potassium • DMF (solvent) •

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