Abstract
In this short review article, we highlight the application of the olefin metathesis reaction as a key step in the total synthesis of (-)-kendomycin, a macrocyclic polyketide ansamycin exhibiting pronounced activity as an endothelin receptor antagonist and antiosteoporotic agent, as well as important antibiotic potency against multiresistant bacteria and remarkable cytotoxicity versus a series of human tumour cell lines. By selecting this example from the recent literature, we hope to illustrate the great synthetic ability of olefin metathesis, while also revealing some problems encountered in the syntheses.
Keywords: Homogeneous catalysis, kendomycin, macrocyclisation, olefin metathesis, polyketide, ruthenium catalysts
Current Organic Synthesis
Title:Olefin Metathesis as Key Step in the Synthesis of Bioactive Compounds: Challenges in the Total Synthesis of (-)-Kendomycin
Volume: 9 Issue: 3
Author(s): Dario Bicchielli, Yannick Borguet, Lionel Delaude, Albert Demonceau, Ileana Dragutan, Valerian Dragutan, Morgan Hans, Christo Jossifov, Francois Nicks and Quentin Willem
Affiliation:
Keywords: Homogeneous catalysis, kendomycin, macrocyclisation, olefin metathesis, polyketide, ruthenium catalysts
Abstract: In this short review article, we highlight the application of the olefin metathesis reaction as a key step in the total synthesis of (-)-kendomycin, a macrocyclic polyketide ansamycin exhibiting pronounced activity as an endothelin receptor antagonist and antiosteoporotic agent, as well as important antibiotic potency against multiresistant bacteria and remarkable cytotoxicity versus a series of human tumour cell lines. By selecting this example from the recent literature, we hope to illustrate the great synthetic ability of olefin metathesis, while also revealing some problems encountered in the syntheses.
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Cite this article as:
Bicchielli Dario, Borguet Yannick, Delaude Lionel, Demonceau Albert, Dragutan Ileana, Dragutan Valerian, Hans Morgan, Jossifov Christo, Nicks Francois and Willem Quentin, Olefin Metathesis as Key Step in the Synthesis of Bioactive Compounds: Challenges in the Total Synthesis of (-)-Kendomycin, Current Organic Synthesis 2012; 9 (3) . https://dx.doi.org/10.2174/157017912801270586
DOI https://dx.doi.org/10.2174/157017912801270586 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
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