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Synthesis of Longifolene
Longifolene
 A naturally occurring, oily liquid hydrocarbon found
primarily in the high-boiling fraction of certain pine resins.
 The name is derived from that of a pine species from which
the compound was isolated, Pinus longifolia.
 Compact tricyclic structure and lack of functional groups.
 Attractive target for research groups highlighting new
synthetic methodologies.
 Notable syntheses are by Corey, McMurray, Johnson,
Oppolzer, and Schultz.
Retrosynthesis
Synthesis of Longifolene
Retrosynthesis
W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583 –
2584
De Mayo reaction
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Synthesis of Longifolene through retrosynthestic analysis.