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

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

Volume: 9 Issue: 6

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

Affiliation:

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

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.

Cite this article as:

Demonceau Albert, Dragutan Ileana, Dragutan Valerian and Le Gendre Pierre, Olefin Metathesis as Key Step in the Synthesis of Bioactive Compounds: Challenges in the Total Synthesis of Iriomoteolides, Current Organic Synthesis 2012; 9 (6) . https://dx.doi.org/10.2174/157017912803901637