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Total Synthesis of (±)-Longifolene Yiyun Peng March 4th, 2013 W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583 – 2584.

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Presentation on theme: "Total Synthesis of (±)-Longifolene Yiyun Peng March 4th, 2013 W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583 – 2584."— Presentation transcript:

1 Total Synthesis of (±)-Longifolene Yiyun Peng March 4th, 2013 W. Oppolzer, T. Godel, J. Am. Chem. Soc. 1978, 100, 2583 – 2584

2 Professor Wolfgang Oppolzer Biography:  1937 Born in Vienna, Austria  1960 Diploma at the University of Vienna  Dr. sc. techn. at ETH, Zürich with Vladimir Prelog  Postdoc at Harvard University, with E.J. Corey  Postdoc at the Woodward Research Institute, Basel. with R.B. Woodward  Research chemist at Sandoz company  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 Tetrahedron - 6 Angewandte Chemie

3 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.

4 [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 Retrosynthesis De Mayo reaction

5 [1] Oppolzer, W.; Godel, T. J. Am. Chem. Soc. 1978, 100, [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 Forward Synthesis (±)-Longifolene

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