ntramolecular Enone-Olefin Photocycloadditions Directed Toward Natural Product Synthesis Travis dunn DAE Group Friday Afternoon Seminar March 31. 2000 Lead References. a Intramolecular Enone-Olefin Photocycloaddition Crimmins. M.T. Chem. Rev. 1988. 88. 1453-1473 a Cycloaddition/Fragmentation Strategies in Synthesis Winkler, J D. et al. Chem. Rev. 1995. 95. 2003-2020 Mechanism of Enone-Olefin Photocycloadditic Introduction and scope D)Mechanistic considerations of the enone-olefin photocycloaddition II) Selected synthetic examples A) The Oppolzer syntheses B)The Pattenden syntheses C)The Pirrung syntheses D)One hit wonders E)The Crimmins syntheses F)The Winkler syntheses The following will not be covered in this seminar Non-target motivated studies of the intramolecular photocycloaddition II)Intramolecular Paterno-Buchi reactions Ill)Intramolecular ketene cycloadditions IV)Other intramolecular photocycloadditions(e.g. arene-olefin meta cycloadditions) 36A-01 handout3/31/001:29PMIntramolecular Enone-Olefin Photocycloadditions Directed Toward Natural Product Synthesis Travis Dunn DAE Group Friday Afternoon Seminar March 31, 2000 O O hν Lead References: ■ Intramolecular Enone-Olefin Photocycloaddition Crimmins, M.T. Chem. Rev. 1988, 88, 1453-1473. ■ Cycloaddition/Fragmentation Strategies in Synthesis Winkler, J.D., et al. Chem. Rev. 1995, 95, 2003-2020. ■ Mechanism of Enone-Olefin Photocycloaddition Schuster, D.I., et al. Chem. Rev. 1993, 93, 3-22. Introduction and Scope I) Mechanistic considerations of the enone-olefin photocycloaddition II) Selected synthetic examples: A) The Oppolzer syntheses B) The Pattenden syntheses C) The Pirrung syntheses D) One hit wonders E) The Crimmins syntheses F) The Winkler syntheses The following will not be covered in this seminar: I) Non-target motivated studies of the intramolecular photocycloaddition II) Intramolecular Paterno-Büchi reactions III) Intramolecular ketene cycloadditions IV) Other intramolecular photocycloadditions (e.g. arene-olefin meta cycloadditions) 36A-01-Handout 3/31/00 1:29 PM