"Enabling Access to Diverse Bioactive Molecules Through Enyne Metathesis Concepts"

Ileana Dragutan, Valerian Dragutan, Albert Demonceau, and Lionel Delaude

journal cover
          source: Current Organic Chemistry
            year: 2013
          volume: 17
      first page: 2678
       last page: 2720
             doi: 10.2174/13852728113179990113

Abstract: This paper surveys recent advances in valorization of transition-metal-catalyzed enyne metathesis as key events in the total synthesis of naturally occurring compounds of biological and medicinal importance. Special attention is devoted to methodologies based on dienyne ring-closing metathesis (RCM) applied in tandem and sequential processes, on relay ring-closing metathesis (RRCM), ring-rearrangement metathesis (RRM), enyne cross-metathesis (CM) and enyne skeletal bond reorganization, all proceeding under metal-carbenes (Ru or Mo alkylidenes) or metal-salts (Pd or Pt) catalysis. The high potential of these procedures in constructing versatile scaffolds as essential structural cores of a diversity of bioactive natural products is highlighted. Inventive functionalizations by non-metathesis transformations intervening in the total synthesis of the targeted natural compounds, prior to (Michael addition, Wittig olefination, allylation etc) or after (Diels-Alder cycloaddion, Heck and Suzuki-Miyaura reactions, Dess-Martin oxidation, dihydroxylation, epoxidation etc) the pivotal metathesis step have also been included.

Keywords: Bioactive Natural Compounds, Cross-Metathesis, Enyne Metathesis, Relay Ring-Closing, Ring-Closing Metathesis, Ring-Rearrangement Metathesis, Ruthenium Catalysts, Skeletal Bond Reorganization, Tandem Processes

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