Total synthesis of Kempene-2 (Dauben):
| Reference: | Dauben, W. G.; Farkas, I.; Bridon, D. P.; Chuang, C. P.; Henegar, K. E. J. Am. Chem. Soc. 1991, 113, 5883. DOI |
| Reactions: | Li-Ether+Ketone • Li/H → Li-Ether • Diels-Alder, Quinone • Bicyclo(440) • Ketone → Alkyl-OH • CompRed-Ketone/Ketone+M-H • Peterson → Enol ether • Reductive formylation • Wittig-methyl • Aldol-Acid → Enone • Cyclopentene • Ether-8 • Bicyclo(430) • McMurry coupling → Ene • Cycloheptane • Diol-1,2 cleavage • Alkene cleavage • Diels-Alder, Enone • Bicyclo(440) • Enone → Ketone • O-H → O-Bn • Hydroboration → Alkyl-OH • CompRed-Alkene/Alkene+M-H • O-H → O-Bn • Hydroboration → Alkyl-OH • Alkyl-OH → Ketone • Ketone → Ketone-α-Halo • Ketone-α-Halo → Enone • Dehydrohalogenation → Enone • Alkene → Diol-1,2 • O-Bn → O-H • O-H → O-C(O)R • EnolEther → Ketone • Alkyl-OH → Aldehyde • EnolEther → Aldehyde • |
| Reagents: | BF3·OEt2 • Zn° • BH(sBu3)-Li+ • H2O2, NaOH • NaH • Benzyl-X • Iodide, R4N+ • BuLi(sec) • Formic acid • PPh3=CH2 • KOtBu • BH(Siam)2 • H2O2, NaOH • NaH • BH3 • DMSO, (COCl)2 (Swern) • Tribromide • Carbonate, lithium • OsO4 • NMe3(O) • H2, Pd • Periodate, sodium • TsOH • Acetic anhydride, DMAP • HCl, EtOH • Al2O3 • TiCl3, Zn/Cu • Butadiene • AlEtCl2 • Butadiene • Benzyl-X • |