Total Synthesis of (±)- Longifolene

Total Synthesis of (±)-Longifolene YiyunPeng 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 • 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 AngewandteChemie • Research Interests: • stereocontrolledcycloaddition and cyclization reactions • - DA-rx, • - ene-rx, • - 1,3-dipolar-additions, • - electrocyclicringclosures; • 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, Pinuslongifolia. • 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. Acta1984, 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. Acta1984, 67, 1154; For successful total syntheses of longifolene, see Corey et al. J. Am. Chem. Soc. 1964, 86, 5570

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Total Synthesis of (±)- Longifolene