Total synthesis of Jatrophone:
| Reference: | Han, Q.; Wiemer, D. F. J. Am. Chem. Soc. 1992, 114, 7692-7697. DOI.Becicka, B. T.; Koerwitz, F. L.; Drtina, G. J.; Baenziger, N. C.; Wiemer, D. F. J. Org. Chem., 1990, 55, 5613–5619. DOI |
| Reactions: | O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • Li-Phosphonate+CarboxEster • O-H → O-C(O)R • HWE → EnoateEster (intram) • HWE → EnolEther • Cyclopentenone • Ether-5 • Spiro(44)-oxa • Allyl-OH → Enal • Li-Alkynyl+Aldehyde • Li/H → Li-Alkynyl • Cyclododecane • Allyl-OH → Enone • Propargyl-OH → Ynone • Alkyne → Ene-cis (Lindlar) • Alkene isomerization-EZ • Pd/Sn-Vinyl+Vinyl-X • Dieckmann • CarboxEster enolate+CarboxEster • Ketone → EnolSilane • Ketone → Ketone-α-OR • O-H → O-SiMe3 • Ketone → EnolTriflate • Carbocupration Alkyne • Mg-R → Cu-R • Cu-Vinyl+I2 • Li/I → Li-Vinyl • Li-R → Sn-R • |
| Reagents: | Me-MgBr • CuI • I2 • SiMe2tBu-Cl • Vinyl-I • BuLi(n) • SnMe3-Cl • Vinyl-SnR3 • P(O)(OR)2CH2-Alkyl • LiN(SiMe3)2 • FeCl3 • NaH • Pd(PPh3)4 • Iodide, potassium • Fluoride, R4N+ • LiN(SiMe3)2 • DMSO, (COCl)2 (Swern) • H2, Pd • Iodide, potassium • OsO4, NMO • Fluoride, R4N+ • SiMe3-Cl • LiNiPr2 • Tf2NPh • DMSO, (COCl)2 (Swern) • Imidazole • |