Abstract
The regioselective synthesis of the 3,4,5-trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl)benzaldehyde as key intermediate for divergent preparation of cytotoxic biaryl lignans was achieved in three steps from commercially available starting materials. Reactivity of this synthon was illustrated by its conversion into the corresponding phenanthridine and bromomethylbenzene.
Keywords: Carbaldehydes, cytotoxic biaryls, lignans, phenanthridines, regioselective nitration, stille coupling, biphenyl, antitumor drugs, steganone, eupomatilone-6.
Letters in Organic Chemistry
Title:Synthesis of the 3,4,5-Trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for Divergent Preparation of Cytotoxic Biaryls
Volume: 9 Issue: 8
Author(s): Raphael Labruere, Philippe Helissey, Stephanie Desbene-Finck and Sylviane Giorgi-Renault
Affiliation:
Keywords: Carbaldehydes, cytotoxic biaryls, lignans, phenanthridines, regioselective nitration, stille coupling, biphenyl, antitumor drugs, steganone, eupomatilone-6.
Abstract: The regioselective synthesis of the 3,4,5-trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl)benzaldehyde as key intermediate for divergent preparation of cytotoxic biaryl lignans was achieved in three steps from commercially available starting materials. Reactivity of this synthon was illustrated by its conversion into the corresponding phenanthridine and bromomethylbenzene.
Export Options
About this article
Cite this article as:
Labruere Raphael, Helissey Philippe, Desbene-Finck Stephanie and Giorgi-Renault Sylviane, Synthesis of the 3,4,5-Trimethoxy-2-(3,4-methylenedioxy-6-nitrophenyl) benzaldehyde for Divergent Preparation of Cytotoxic Biaryls, Letters in Organic Chemistry 2012; 9 (8) . https://dx.doi.org/10.2174/157017812802850276
DOI https://dx.doi.org/10.2174/157017812802850276 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
- 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
-
Synthesis, Characterization, Biological Activity and Voltammetric Behavior and Determination of Cefaclor Metal Complexes
Current Analytical Chemistry Emerging Vascular Risk Factors in Women: Any Differences from Men?
Current Medicinal Chemistry Steroid Regulation of Drug-Metabolizing Cytochromes P450
Current Drug Metabolism A Survey of Kidney Segmentation Techniques in CT Images
Current Medical Imaging Anthracyclines-Contra Cruciform Extrusion in DNA Regulating Sequences
Endocrine, Metabolic & Immune Disorders - Drug Targets Synthesis of 3-(2, 8, 9-trioxa-5-aza-1-germatricyclo [3.3.3.0] Undecane-1- yl)-3-(4-hydroxyl-3-methoxyphenyl)-propionic Acid and its Inhibitory Effect on the Cervical Tumor U14 in vitro and in vivo
Medicinal Chemistry Synergistic Inhibition of R5 HIV-1 by the Fusion Protein (FLSC) IgG1 Fc and Maraviroc in Primary Cells: Implications for Prevention and Treatment
Current HIV Research In-Vitro CYP3A4, CYP2E1 and UGT Activity in Human Liver Microsomes by Strobilanthes crispus Leaf Extracts
The Natural Products Journal Two Novel GPER Agonists Induce Gene Expression Changes and Growth Effects in Cancer Cells
Current Cancer Drug Targets Analgesic Prodrugs for Combating their Side-Effects: Rational Approach
Current Drug Delivery Phosphocitrate, A Potential Therapeutic Agent for Calcium Crystal Deposition Diseases
Current Rheumatology Reviews Vitamin D and the Metabolic Syndrome
Current Vascular Pharmacology Computer-Aided Drug Design Applied to Secondary Metabolites as Anticancer Agents
Current Topics in Medicinal Chemistry Bioinspired Microchip Nanoporous Interferometric Sensor for Sensing and Biosensing Applications
Micro and Nanosystems Nutritional and Medical Applications of Spirulina Microalgae
Mini-Reviews in Medicinal Chemistry Iron Chelators in Cancer Chemotherapy
Current Topics in Medicinal Chemistry Review of Chemoradiotherapy for High-Risk Prostate Cancer
Reviews on Recent Clinical Trials Design, Synthesis and Docking study of Novel Imidazolyl Pyrazolopyridine Derivatives as Antitumor Agents Targeting MCF7 Cell Line
Current Organic Synthesis Analytical Tools for Detecting Amyloid Beta Oligomerisation and Assembly
Current Pharmaceutical Analysis Targeting 5-Lipoxygenase for Prevention and Treatment of Cancer
Current Enzyme Inhibition