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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 (Swern) • PPh3=CH2 • DMSO, (COCl)2 (Swern) • Fluoride, R4N+ • Vinyl-ZnX • Pd(PPh3)4 • Carbonate, potassium • DMF (solvent) •

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