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FUNCTIONALIZATION OF THE BENZOBICYCLO[3.2.1]OCTADIENE SKELETON

Many new rigid polycyclic structures 1-5 was obtained by photochemical cycloadditions of conjugated furan and butadiene systems in only one step, having benzobicyclo[3.2.1]octadiene skeleton.1 Exactly this skeleton represents the basic structural unit of the great number of important biologically active natural compounds.2 To achieve that objective, great intention was focused to the stereoselective formation of this structure3 and also to the determination of the relative stereochemistry on that bridged bicyclic system.4 Although the reactions of variously substituted bicyclo[3.2.1]octadiene structure has been thoroughly investigated, there is a need for new synthetic pathways concerning the biological activity of related functional derivatives. For that reason, various transformations were carried out on the benzobicyclic structures 1-5 obtained by photochemical methodology, 1 posessing furan ring or a double bond functionality for further transformations. Functionalization of this type of skeleton has been performed by oxidation and addition reactions to obtaine novel reactive and water-soluble derivatives. 1. I. Škorić, M. Šmehil, Ž. Marinić, K. Molčanov, B. Kojić-Prodić, M. Šindler-Kulyk, J. Photochem. Photobiol. A 207 (2009) 190–196 and references therein ; D. Vidaković, I. Škorić, M. Horvat, Ž. Marinić, M. Šindler-Kulyk, Tetrahedron 64 (2008) 3928–3934 ; I. Škorić, N. Basarić, Ž. Marinić, A. Višnjevac, B. Kojić-Prodić, M. Šindler-Kulyk, Chem. Eur. J. 11 (2005) 543–551. 2. L. N. Mander, Chem. Rev. 92 (1992) 573-612 ; H. Lin, S. J. Danishefsky, Angew. Chem. Int. Ed. 42 (2003) 36-51 ; H. Nagata, M. Kawamura, K. Ogasawara, Synthesis 13 (2000) 1825- 1834. 3. M.-H. Filippini, J. Rodriguez, Chem. Rev. 99 (1999) 27-76 ; P. Langer, E. Holtz, N. N. R. Saleh, Chem. Eur. J. 8 (2002) 917-928. 4. O. V. Patrusheva, G. A. Verbitskii, V. I. Vysotskii, Tetrahedron 60 (2004) 1761-1766.

benzobicyclo[3.2.1]octadiene; cycloadditions; functionalization; photochemistry

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