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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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 and Pierre Le Gendre

Volume 9, Issue 6, 2012

Page: [779 - 790] Pages: 12

DOI: 10.2174/157017912803901637

Price: $65

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.


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