Total synthesis of Nakienone B:
| Reference: | Pour, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 4679. DOI |
| Reactions: | Luche reduction • Enone → Allyl-OH • O-H → O-SiMe3 • O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Birch reduction • Wittig-methyl → Diene • Li/I → Li-Vinyl • CompE+-Vinyl-I/RO-SiMe3+M-R • Alkyne Hydroalumination • Li-Alkynyl+Aldehyde • Enone → Enone-α-Halo • Epoxide → Allyl-OH • Pd/Zn-Vinyl+Vinyl-X • EnolEther → Ketone • O-H → O-SiMe2tBu • Li-R → Zn-R • Li/H → Li-Alkynyl • Al-Vinyl → I-Vinyl • Alkyne → Vinyl-I • Allyl-OH → Enal • Allyl-OH → Enone • Epoxidation, peracid • O-SiMe3 → O-H • |
| Reagents: | Li°/NH3 • SiMe2tBu-Cl • I2, Py • BH4-Na+, CeCl3 • SiMe3-Cl • Vinyl-Li • 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) • Al2O3 • Perbenzoic acid, 3-chloro • |