Stereochemical assignment of alcohols in total synthesis of (-)-aureonetol
Journal name: World Journal of Pharmaceutical Research
Original article title: Steriochemical assignment of alcohols –a versatile chiral building blocks studies towards total synthesis of (-)-aureonetol
The WJPR includes peer-reviewed publications such as scientific research papers, reports, review articles, company news, thesis reports and case studies in areas of Biology, Pharmaceutical industries and Chemical technology while incorporating ancient fields of knowledge such combining Ayurveda with scientific data.
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Govind Jadhav, Prasad Kadam, Ganpat Nagargoje, Abhay Bondge, Shital Jadhav, Vijaykumar More
World Journal of Pharmaceutical Research:
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Full text available for: Steriochemical assignment of alcohols –a versatile chiral building blocks studies towards total synthesis of (-)-aureonetol
Source type: An International Peer Reviewed Journal for Pharmaceutical and Medical and Scientific Research
Doi: 10.20959/wjpr20238-28240
Copyright (license): WJPR: All rights reserved
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Summary of article contents:
Introduction
The increasing global concern regarding multidrug-resistant microbes and the environmental impact of synthetic production has driven significant interest in alternative methods for the discovery and production of valuable pharmaceutical compounds. This study focuses on the synthesis and significance of (-)-Aureonetol, a tetrahydrofuran derivative known for its antiviral properties against influenza. The research outlines innovative synthetic strategies and highlights the importance of understanding the structural intricacies of the target compound and its related analogs.
Tetrahydrofuran and Its Importance
Tetrahydrofuran (THF) sub-units are prevalent in numerous natural products, presenting a challenge for their synthetic accessibility. The Chaetomium genus of fungi has emerged as a notable source of structurally diverse metabolites, including Aureonetol. This compound inhibits viral infections by targeting hemagglutinin, a crucial glycoprotein on the influenza virus's surface. The study underscores the significance of THF derivatives due to their bioactive potential, particularly in pharmacology, where they demonstrate a range of effects, including anticancer and antimicrobial activities.
Novel Synthetic Strategies
The synthesis of (-)-Aureonetol involves a series of advanced synthetic strategies, notably the Wittig olefination and Claisen rearrangement. The process begins with the formation of allyl vinyl ethers from aldehydes or ketones, leading to the generation of 4-pentenal, a critical intermediate. The research documents the careful orchestration of reactions yielding high product yields, including the separation of diastereomers and alcohol forms. This illustrates both the ingenuity required for constructing complex structures and the potential for optimization in synthetic methodology.
Stereochemical Assignments
Establishing the absolute stereochemistry of the resultant alcohols is an essential aspect of the study, achieved through chemical correlation with known compounds. The comparative analysis of optical rotations of synthesized alcohols with those of established analogs allowed for the accurate assignment of stereochemical configurations. This critical step in synthesis not only confirms the structure of the final products but also furthers the understanding of chiral center formation during complex chemical processes.
Conclusion
The research demonstrates that while current synthetic routes to (-)-Aureonetol employ innovative methods, there remains ample opportunity for enhancing these strategies. The utilization of Wittig olefination followed by Claisen rearrangement has proven effective in various natural product syntheses. Future efforts may focus on refining these approaches to achieve greater efficiency, ultimately contributing to the broader goal of discovering and producing pharmacologically relevant compounds with significant therapeutic potential, such as (-)-Aureonetol.
FAQ section (important questions/answers):
What is the main focus of the study on Aureonetol?
The study focuses on developing efficient synthetic strategies for Aureonetol, a tetrahydrofuran derived from fungi, noted for its antiviral properties against influenza.
What synthetic methods were employed in synthesizing (-)-Aureonetol?
The synthesis involved Wittig olefination of aldehydes/ketones to obtain allyl vinyl ethers, followed by a Claisen rearrangement to generate 4-pentenal.
What are the two main alcohol products identified in the study?
The two main alcohols obtained are less polar alcohol 6 and more polar alcohol 7, resulting from the reduction of a diastereomeric mixture of 4-pentenal.
How was the stereochemistry of alcohols 6 and 7 determined?
The stereochemistry was determined by comparing their optical rotations with known compounds prepared by Kishi et al.
What biological activity is associated with Aureonetol?
Aureonetol exhibits antiviral activity by inhibiting influenza replication, specifically targeting the hemagglutinin glycoprotein on the virus.
What further applications are suggested for the synthetic approaches discussed?
The study suggests potential applications of the existing synthetic protocols in the synthesis of various natural products beyond Aureonetol.
Glossary definitions and references:
Scientific and Ayurvedic Glossary list for “Stereochemical assignment of alcohols in total synthesis of (-)-aureonetol”. This list explains important keywords that occur in this article and links it to the glossary for a better understanding of that concept in the context of Ayurveda and other topics.
1) Water:
Water is essential for life and is often involved in various chemical reactions within biological systems. In the context of pharmaceutical research, the solvent properties of water are crucial for the solubility of compounds and the efficient execution of reactions, affecting yields and effectiveness in natural products synthesis.
2) Genu:
Genu refers to the knee or bend and is used in anatomical descriptions. Although not directly relevant to pharmaceutical research, understanding bodily anatomy and physiology is crucial for drug formulation and therapeutic interventions in fields like orthopedics and rehabilitative medicine, highlighting the body’s structures where drugs may interact.
3) Species:
A species is the most basic unit in biological classification, representing a group of organisms capable of interbreeding. Identifying species is fundamental in pharmaceutical research as it helps in isolating compounds with potential medicinal properties, informing taxonomy and ecological interactions that can lead to new drug discoveries.
4) Activity:
Activity, in a pharmaceutical context, refers to the biological effect or efficacy of a compound or drug in inducing a specific response in living organisms. Understanding the activity is essential for evaluating potential therapeutics, optimizing drug design, and ensuring safety and effectiveness in clinical applications.
5) Hand:
The term 'hand' can metaphorically represent manual dexterity or the ability to manipulate tools. In laboratory settings, precise handling of instruments and compounds is critical for successful chemical syntheses. This skill is paramount in pharmaceutical research to maintain accuracy and reproducibility in experiments.
6) Transformation (Transform, Transforming):
Transform refers to the change in structure or function of a compound during a chemical reaction. In pharmaceutical synthesis, transforming one compound into another is a key aspect of drug development that allows scientists to create novel molecules with desired biological activities through various chemical processes.
7) Rasika (Rashika):
Rasika is potentially a name associated with a specific educational institution or an individual in this context. Understanding the contribution of researchers or institutions is significant in the advancement of scientific knowledge, as their work may lead to new discoveries in pharmaceutical chemistry and related fields.
8) Reason:
The reason is the basis or rationale behind actions or decisions. In scientific research, providing clear reasons for experimental designs, data interpretations, and conclusions is vital for credibility and reproducibility, allowing other researchers to understand the logic behind findings and to build on previous work.
9) Drug:
A drug is any substance used to diagnose, cure, treat, or prevent disease. In pharmaceutical research, understanding drug discovery, development, and mechanisms of action is essential for creating effective therapies, addressing public health needs, and advancing medical science in treating various diseases and health conditions.
10) Soil:
Soil is a natural resource that provides habitat for various organisms. In pharmaceutical research, soil can be a source of diverse microbial and plant species, which may yield bioactive compounds with potential therapeutic effects, driving exploration for novel natural products with medicinal properties.
11) Purification:
Purification involves the removal of impurities or unwanted components from a substance. In pharmaceutical contexts, purification is critical for isolating desired compounds from natural sources or during drug synthesis, directly impacting the safety, efficacy, and quality of pharmaceutical products for human use.
12) Cosmopolitan (Cosmopolitanism):
Cosmopolitan describes organisms widely distributed across various regions and environments. The study of cosmopolitan species in pharmaceutical research is important, as these species may contain bioactive compounds relevant to human health. Their adaptability and prevalence may indicate valuable potential for drug discovery.
13) Discussion:
Discussion refers to the critical analysis and interpretation of research findings. In scientific publications, thorough discussions provide insights into the implications of results, exploring limitations, potential applications, or future research directions, fostering greater understanding and encouraging further inquiry in pharmaceutical studies.
14) Developing:
Developing refers to the process of advancing or creating new methods, substances, or ideas. In pharmaceutical research, developing new drugs or formulations is a complex journey involving synthesis, testing, and optimization to effectively address health concerns and improve therapeutic outcomes.
15) Mineral:
Minerals are naturally occurring inorganic substances that play essential roles in biological systems. In pharmaceuticals, minerals can be critical either as active ingredients in drugs (like calcium) or as catalysts in chemical reactions during drug synthesis, highlighting their importance in health and disease mitigation.
16) Surface:
Surface refers to the outermost layer of a material or organism. In pharmaceutical research, surface interactions can be significant in drug delivery systems, where the surface properties of nanoparticles or drug formulations can affect dissolution rates, bioavailability, and targeted delivery effectiveness in therapeutic applications.
17) Cancer:
Cancer represents a group of diseases characterized by uncontrolled cell growth. Research in oncology is crucial for discovering new treatments and understanding cancer's biological mechanisms. Pharmaceutical research focuses on developing targeted therapies, improving early detection, and enhancing patients' quality of life through innovative drug formulations.
18) Nature:
Nature refers to the natural world and its ecosystems. In pharmaceutical research, many medicines are derived from natural products sourced from plants, fungi, or microorganisms. Understanding nature’s chemistry encourages sustainable practices and the exploration of biodiversity for discovering novel therapeutic compounds.
19) Kadam:
Kadam is possibly a name associated with an author or contributor in this context. Recognizing individual contributions in research institutions fosters collaboration and highlights the importance of teamwork in advancing pharmaceutical knowledge and success in drug development and synthesis.
20) Shri (Sr, Sri):
Shri is a title of respect used in India, often preceding names. In the context of academic publications, it indicates esteemed individuals, particularly researchers. Acknowledging titles reflects the cultural context in which scientific work is conducted and promotes respect within academic and professional communities.
21) Rich (Rch):
Rich can describe ecosystems or sources that are abundant with diverse organisms or compounds. In pharmaceutical contexts, richness in biodiversity can lead to the discovery of new drugs, as varied organisms produce unique metabolites with therapeutic potential, making biodiversity important for ongoing drug research.
22) Viru:
Viru may refer to a name or title associated with a person or concept in this context. A proper understanding of individuals linked to research contributes to the recognition of teamwork and collaborative efforts behind scientific advancements, fostering a culture of respect and encouragement within the scientific community.
Other Science Concepts:
Discover the significance of concepts within the article: ‘Stereochemical assignment of alcohols in total synthesis of (-)-aureonetol’. Further sources in the context of Science might help you critically compare this page with similair documents:
Anticancer activity, Anti-cancer activity, Secondary metabolite, Elemental analysis, NMR spectrum, Bioactive natural products, IR spectrum, Wittig reaction, Multidrug resistant microbes, Synthetic strategies, Oxidative cleavage, Specific Optical Rotation, Chiral building blocks, Tetrahydrofuran sub-unit, Wittig olefination, Claisen rearrangement, Aureonetol synthesis, Allyl vinyl ethers, Pharmacologically important molecules, Chaetomium species, Synthesis of natural products, Cyclohexyl group, Diastereomeric mixture, Benzyl ether, Transcriptional regulator, STEREOCHEMICAL ASSIGNMENT OF ALCOHOLS, ALCOHOLS –A VERSATILE CHIRAL BUILDING BLOCKS, DICYCLoHEXYLIDENE PROTECTION, TOTAL SYNTHESIS OF (-)-AUREONETOL, CHAETOMIUM GENUS, INFLUENZA REPLICATION, SPECTRAL VALUES AND ANALYTICAL DATA, DIAStereOISOMERS.