Total synthesis of Longipinene:
| Reference: | Masaaki, M.; Yoshikoshi, A. J. J. Am. Chem. Soc. 1974, 96, 1917–1925. DOI |
| Reactions: | Epoxidation, peracid • Henbest • O-H → O-THP • Enone → Allyl-OH • CompRed-Ketone/CarboxEster+M-H • Grob fragmentation • Cyclodecane • O-H → O-SO2Me • CompNu-O-H/O-H+RSO2X • Ketone → Alkyl-OH • O-H → O-C(O)R • O-THP → O-H • Epoxide reduction • Dehydroacetoxylation → Enone • Wittig-methyl → Diene • Photochemistry 2+2 • Cyclobutane • Alkene cleavage • Alkyl-OH → Ketone • Alkene → Diol-1,2 • Sulfonium ylide+Ketone • Epoxidation ylide • Corey-Chaykowsky • Hydrogenation azide • Azide → Amine • Demjanov rearrangement • Epoxide+M-N3 • Li-Me+Ketone • Dehydration → Ene • Ketone → C=CH2 • |
| Reagents: | BH4-Na+ • DHP • POCl3 • Perbenzoic acid, 3-chloro • Sulfonyl chloride, methane, NEt3 • NaH • AlH4-Li+ • Acetyl chloride • TsOH • AlH4-Li+ • CrO3·Py2 (Collins) • Al2O3 • PPh3=CH2 • OsO4 • Periodic acid • Me2S=CH2 • Azide, sodium • H2, Pt • Nitrite, sodium • Me-Li • POCl3 • |