Total synthesis of Longifolene (Corey):
| Reference: | Corey, E. J.; Ohno, M.; Mitra, R. B.; Vatakencherry, P. A. J. Am. Chem. Soc. 1964, 86, 478. DOI |
| Reactions: | Wittig-alkyl+Ketone • Alkene → Diol-1,2 • O-H → O-SO2Ar • CompNu-O-H/O-H+RSO2X • Semipinacol • Cycloheptane • Bicyclo(540) • ConjAdd Enolate • Ketone enolate+Enone • Bicyclo(221) • Hydrogenolysis C-S • Ketone → CH2 • Alkyl-SR → Alkyl-H • Ketone enolate+Me-I • Ketone → Ketal • CompE+-Ketone/Ketone+glycol • Ketal → Ketone • Alkene isomerization • Ketone → Ketal(thio) • Ketone → Alkyl-OH • Alkyl-OH → Ketone • Li-Me+Ketone • Ketone+Li-Alkyl • Dehydration → Ene • Ketone → C=CH2 • |
| Reagents: | Wieland-Miescher • Glycol • TsOH • PPh3=CH-Me • OsO4 • TsCl, Py • LiClO4 • Carbonate, calcium • HCl, H2O • NEt3 • NaCPh3 • MeI • Thiol, (CH2)2-SH • BF3·OEt2 • AlH4-Li+ • Hydrazine • CrO3 • Me-Li • SOCl2 • |