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

Author(s): Albert Demonceau, Ileana Dragutan, Valerian Dragutan, Pierre Le Gendre

Journal Name: Current Organic Synthesis

Volume 9 , Issue 6 , 2012

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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.

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Article Details

Year: 2012
Page: [779 - 790]
Pages: 12
DOI: 10.2174/157017912803901637
Price: $65

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