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Olefin Metathesis as Key Step in the Synthesis of Bioactive Compounds: Challenges in the Total Synthesis of Iriomoteolides

[ Vol. 9 , Issue. 6 ]

Author(s):

Albert Demonceau, Ileana Dragutan, Valerian Dragutan and Pierre Le Gendre   Pages 779 - 790 ( 12 )

Abstract:


Iriomoteolides are novel macrolides possessing either a unique 15-membered or a 20-membered macrocycle, and displaying exceedingly potent cytotoxicity with IC50 values of up to 2 ng/mL. Thus far, over a period of about four years, ten research groups worldwide have published their synthetic efforts resulting in four total syntheses of iriomoteolides and a few diastereomers thereof, and a number of fragment and macrocyclic core syntheses. Interestingly, three total syntheses involved ring-closing metathesis as the key step for the construction of the macrocycle, whereas the synthesis of three fragments was accomplished using a cross-metathesis reaction. Herein we highlight assets and limitations of the olefin metathesis reaction in the synthesis of the title compounds.

Keywords:

Homogeneous catalysis, iriomoteolides, macrocyclisation, macrolide, olefin metathesis, ruthenium catalysts.

Affiliation:

Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liege, Sart-Tilman (B.6a), B-4000 Liege, Belgium.



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