Total Synthesis
of (±)-Longifolene
Yiyun Peng
March 4th, 2013
W. Oppolzer, T. Godel, J. Am. Chem. Soc.
1978, 100, 2583 – 2584
Professor Wolfgang Oppolzer
Biography:
 1937 Born in Vienna, Austria
 1960 Diploma at the University of Vienna
 1960-1963 Dr. sc. techn. at ETH, Zürich with
Vladimir Prelog
 1963-1964 Postdoc at Harvard University, with
E.J. Corey
 1965-1967 Postdoc at the Woodward Research
Institute, Basel. with R.B. Woodward
 1967-1973 Research chemist at Sandoz
company
 1974-1996 Professor at the University of
Geneva
Research Interests:
 stereocontrolled cycloaddition and cyclization
reactions
- DA-rx,
- ene-rx,
- 1,3-dipolar-additions,
- electrocyclic ringclosures;
 chiral auxiliaries
Publications:
 author / coauthor on over 200 publications
~ 180 original research papers
~ 80 Helvetica Chim. Acta
~ 70 Tetrahedron Letters
~ 15 J. Am. Chem. Soc.
- 14 Tetrahedron
- 6 Angewandte Chemie
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
De Mayo reaction
[1] Oppolzer, W.; Godel, T. Helv. Chim. Acta 1984, 67, 1154; [2] De Mayo et al., Can. J. Chem. 1963, 41, 440; [3] Corey et al. J.
Am. Chem. Soc. 1964, 86, 5570
Forward Synthesis
(±)-Longifolene
[1] Oppolzer, W.; Godel, T. J. Am. Chem. Soc. 1978, 100, 2583. [2] Oppolzer, W.; Godel, T. Helv. Chim. Acta 1984, 67, 1154;
For successful total syntheses of longifolene, see Corey et al. J. Am. Chem. Soc. 1964, 86, 5570