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:
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.
 Oppolzer, W.; Godel, T. Helv. Chim. Acta 1984, 67, 1154;  De Mayo et al., Can. J. Chem. 1963, 41, 440;  Corey et al. J. Am. Chem. Soc. 1964, 86, 5570 Retrosynthesis De Mayo reaction
 Oppolzer, W.; Godel, T. J. Am. Chem. Soc. 1978, 100, 2583.  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