Total Synthesis of Longifolene by Professor Wolfgang Oppolzer
Learn about the total synthesis of (-)-Longifolene by Yiyun Peng and the contributions of Professor Wolfgang Oppolzer in the field of organic chemistry. Explore the intricate structure and significance of Longifolene as a naturally occurring compound. Discover the Retrosynthesis De Mayo reaction and the forward synthesis of Longifolene, along with notable publications and research interests of Professor Oppolzer.
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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, Z rich 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 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 Research Interests: stereocontrolled cycloaddition and cyclization reactions - DA-rx, - ene-rx, - 1,3-dipolar-additions, - electrocyclic ringclosures; chiral auxiliaries
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
