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Total synthesis of Longipinene:
Reference: Masaaki, M.; Yoshikoshi, A. J. J. Am. Chem. Soc. 1974, 96, 1917–1925. DOI
Keywords: Enone → Allyl-OH • O-H → O-SO2R • Ketone → Alkyl-OH • O-H → O-C(O)R • O-THP → O-H • Alkyl-OH → Ketone • Epoxide+Azide • Epoxidation, peracid • Henbest • O-H → O-THP • Epoxide reduction • Grob fragmentation • Dehydroacetoxylation → Enone • Wittig-methyl • Photochemistry 2+2 • Alkene cleavage • Sulfonium ylide+Ketone • Corey-Chaykowsky • Hydrogenation azide • Azide → Amine • Demjanov rearrangement • Li-Me+Ketone • Dehydration → Ene •
Reagents: BH4-Na+ • Perbenzoic acid, 3-chloro • POCl3 • AlH4-Li+ • Sulfonyl chloride, methane, NEt3 • NaH • AlH4-Li+ • Acetyl chloride • TsOH • CrO3·Py2 (Collins) • Al2O3 • PPh3=CH2 • OsO4 • Periodic acid • Me2S • Azide, sodium • H2, Pt • Nitrite, sodium • MeLi • POCl3

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