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Concise Synthesis of Tricyclic Angularly Fused Natural Products via Controlled Cyclizations of a Common Key Precursor:<br/>Preparation of Alliacanes, Arteannuins, Pentalenolactones and Triquinanes

Final Report Summary - UNIQUE PRECURSOR (Concise Synthesis of Tricyclic Angularly Fused Natural Products via Controlled Cyclizations of a Common Key Precursor:Preparation of Alliacanes, Arteannuins, Pentalenolactones and Triquinanes)

The project State of the Art was to elaborate a novel concept toward the practical synthesis of highly complex and functionalized natural products.
We proposed a general and efficient diversity-oriented synthesis of tricyclic angularly fused-structured natural products via selective cyclization from a common precursor.
During the period of grant, the novel key precursor (of lesser complexity than the target natural products) were designed by simple synthetic sequences.

Project objectives for the period:
1. Design and prepare key precursors - common units for synthesis of structurally related natural products and their analogues.
2. Investigate the mechanism of selective transformations.
3. Utilize the newly designed methodologies as part of our effort to establish diversity-oriented synthetic routes towards a wide variety of natural products.

During the period of our project we aimed to discover and design advanced molecular intermediates able to serve as common platforms for synthesis of various, structurally related (proceeding from same key subunit) compounds – potential therapeutic agents and drug candidates.
Unlike existing classic synthetic “target-directed” methods, our established constructing methodology now offers conceptually new perspective, enabling to deliver multiple targets via sequence of controlled, simple and atom economy reactions from a single common molecular unit; thus, providing simplified access to a wide variety of important classes of biologically active and structurally interesting molecules.
The presence of similar fundamental core structures is not exclusive to chemical compounds extracted from the same natural source. Common or highly resembling structures can be identified throughout various forms of life, such as different (and often distantly related) families of plants, as well as fungi and even bacteria. Several cores (building blocks) were identified, designed and synthesized to have an access to different classes of natural products and important biologically active compounds. The new techniques for the preparation of structurally unique novel molecules were designed as well. All targets and transformations were selected on the basis of novel molecular architecture, important biological activity, and the potential for mechanistic studies.
During the period of grant, we published 3 patents, 4 papers, and the 5th is currently pending with review.
Building upon the foundations of synthetic organic chemistry, the research program of our group invoked a broad interdisciplinary collaboration with other fields such as, medicinal chemistry, organometallic chemistry, biochemistry, pharmacology and medicine.
The start-up funding, I received from the Institute, was be used to equip my laboratory with synthetic and analytical instrumentation. The total space now consists of ~80 square meters (2 labs). My lab includes: 1. Five chemical fume hoods (each equipped with Schlenk line system); 2. Chromatography setup: GC (equipped with FID detector) and ISQ EI-Single Quadruple Mass Spectrometer; 3. Inert atmosphere workstation: Glove box and Solvent Purification System; 4. Chemical refrigerator; 5. Rotovapors; 6. Balances; 7. Ovens; 8. Desiccators; 9. HPLC
During the grant period, I directed the research according to the proposed plan. Most of the basic equipment has been purchased using the start-up funds or provided by the IDR and the Faculty of Medicine. The grant funding supported the special needs of the project, such as supporting students, purchasing special equipment, chemicals and glassware, and participating in the international conferences.

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