"Recent Applications of Alkene Metathesis in Fine Chemical Synthesis"

Dario Bicchielli, Yannick Borguet, Lionel Delaude, Albert Demonceau, Ileana Dragutan, Valerian Dragutan, Christo Jossifov, Radostina Kalinova, François Nicks, and Xavier Sauvage

book cover 
           title: Green Metathesis Chemistry
                  Great Challenges in Synthesis, Catalysis and Nanotechnology
          series: NATO Science for Peace and Security
                  Series A: Chemistry and Biology
         editors: Valerian Dragutan, Albert Demonceau,
                  Ileana Dragutan, Eugene Sh. Finkelshtein
       publisher: Springer
            city: Dordrecht
            year: 2010
      first page: 207
       last page: 274
            isbn: 978-90-481-3431-1 (Print) 978-90-481-3433-5 (Online)
             doi: 10.1007/978-90-481-3433-5_15

Abstract: During the last decade or so, the emergence of the metathesis reaction in organic synthesis has revolutionised the strategies used for the construction of complex molecular structures. Olefin metathesis is indeed particularly suited for the construction of small open-chain molecules and macrocycles using cross-metathesis and ring-closing metathesis, respectively. These reactions serve, inter alia, as key steps in the synthesis of various agrochemicals and pharmaceuticals such as macrocyclic peptides, cyclic sulfonamides, novel macrolides, or insect pheromones. The present chapter is aiming at illustrating the great synthetic potential of metathesis reactions. Shortcomings, such as the control of olefin geometry and the unpredictable effect of substituents on the reacting olefins, will also be addressed. Examples to be presented include epothilones, amphidinolides, spirofungin A, and archazolid. Synthetic approaches involving silicon-tethered ring-closing metathesis, relay ring-closing metathesis, sequential reactions, domino as well as tandem metathesis reactions will also be illustrated.

Keywords: Alkene Metathesis, Cross-Metathesis, Macrocycles, Ring-Closing Metathesis, Ring-Opening Metathesis, Ruthenium Catalysts

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