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.
Current Organic Synthesis
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.
Export Options
About this article
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
DOI https://dx.doi.org/10.2174/157017912803901637 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
Related Articles
-
The Recent Medicinal Chemistry Development of Jak2 Tyrosine Kinase Small Molecule Inhibitors
Current Medicinal Chemistry The Diagnosis of Large Airway Pathology and the Role of Rigid Bronchoscopy
Current Respiratory Medicine Reviews Nanoparticle Drug Delivery Systems: Recent Patents and Applications in Nanomedicine
Recent Patents on Nanomedicine Radiologic Findings of IgG4-Related Disease
Current Immunology Reviews (Discontinued) Preactive Multiple Sclerosis Lesions Offer Novel Clues for Neuroprotective Therapeutic Strategies
CNS & Neurological Disorders - Drug Targets Magnetic Resonance Imaging of Nasopharyngeal Adenoid Hypertrophy in Children Following Bone Marrow Transplantation
Current Medical Imaging Fatty Acids and Effects on In Vitro and In Vivo Models of Liver Steatosis
Current Medicinal Chemistry Angiogenesis and AngiomiRs in Non-Hodgkin´s Lymphomas
Current Angiogenesis (Discontinued) Primary Lung Lymphoma
Current Drug Targets - Inflammation & Allergy Developmental Phases of Anticancer Screening Models
Combinatorial Chemistry & High Throughput Screening Targeting Cancer with Epi-Drugs: A Precision Medicine Perspective
Current Pharmaceutical Biotechnology Editorial [Hot Topic: Targeted Cancer Therapies: Current Status and Future Directions (Guest Editors: Ioannis Starakis)]
Current Medicinal Chemistry Immune Checkpoint Inhibitors for Non-small-cell Lung Cancer: Does that Represent a ‘New Frontier’?
Anti-Cancer Agents in Medicinal Chemistry Imaging of Tumor Angiogenesis: Current Approaches and Future Prospects
Current Pharmaceutical Design Sesbania: A Prospective Candidate to be Excavated for Anticancer Drugs
The Natural Products Journal Yeast as a Powerful Model System for the Study of Apoptosis Regulation by Protein Kinase C Isoforms
Current Pharmaceutical Design Muscular Gene Transfer Using Nonviral Vectors
Current Gene Therapy Glycosaminoglycan Sulodexide Inhibition of MMP-9 Gelatinase Secretion and Activity: Possible Pharmacological Role Against Collagen Degradation in Vascular Chronic Diseases
Current Vascular Pharmacology Three Musketeers for Lowering Cholesterol: Statins, Ezetimibe and Evolocumab
Current Medicinal Chemistry The Mouse In Cancer Research Past, Present, Future
Current Genomics