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Projects / Programmes source: ARRS

Synthesis of heterocyclic amino acid analogues as intermediates in the synthesis of natural products

Research activity

Code Science Field Subfield
1.04.00  Natural sciences and mathematics  Chemistry   

Code Science Field
P003  Natural sciences and mathematics  Chemistry 
Keywords
Indole alkaloids, 1,3-dipolar cycloadditions, azomethine imines, asymmetric synthesis, combinatorial and parallel synthesis, heterocyclic amino acids
Evaluation (rules)
source: COBISS
Researchers (9)
no. Code Name and surname Research area Role Period No. of publicationsNo. of publications
1.  29401  PhD Jernej Baškovč  Natural sciences and mathematics  Junior researcher  2008 - 2011  21 
2.  22602  PhD Uroš Grošelj  Natural sciences and mathematics  Researcher  2008 - 2011  418 
3.  17140  Tončka Kozamernik-Hudeček    Technician  2008 - 2011 
4.  29400  PhD Črt Malavašič  Natural sciences and mathematics  Junior researcher  2008 - 2011  23 
5.  00868  PhD Branko Stanovnik  Natural sciences and mathematics  Principal Researcher  2008 - 2011  1,773 
6.  08284  PhD Jurij Svete  Natural sciences and mathematics  Researcher  2008 - 2011  856 
7.  17142  Tatjana Toporiš Stipanovič    Technician  2008 - 2011 
8.  25443  PhD Uroš Uršič  Natural sciences and mathematics  Junior researcher  2008 - 2009  28 
9.  26548  PhD Jernej Wagger  Natural sciences and mathematics  Researcher  2008 - 2011  60 
Organisations (1)
no. Code Research organisation City Registration number No. of publicationsNo. of publications
1.  0103  University of Ljubljana, Faculty of Chemistry and Chemical Technology  Ljubljana  1626990  22,064 
Abstract
a. Program of the project "Synthesis of heterocyclic analogues of amino acids as intermediates in the syntesis of natural products" consists of several topics: b. 1. Synthesis of chiral enaminones, based on "ex-chiral pool" transformation of enantiomerically pure reagents prepared from amino acids, sugars and terpenes into the compounds with two structural motives: c. -the enaminone or analogous structural element, from which a heterocyclic ring can be formed in the following steps, and d. -functional, which is usually not transformed but rather used as a chiral auxilliary or stereodirecting group influencing the stereoselectivity in further transformations. e. f. 2. Reactions of enaminones and related compounds, especially terpene derivatives, with organometallic compounds, such as organomagnesium, organozinc and organolitium compounds. These reaction represent a novel general synthetic method for the introduction of various C-substitutents, such as alkyl, alkenyl, alkinyl, aryl and heteroaryl, to the polarised conjugated C=C bond. The results of these studies could be then applied to development of new synthetic methodologies for preparation of substituted alpha,beta-unsaturated carbonyl compounds and esters, didehydroalanines and their chiral cyclic analogues, and analogues of natural products such as aplysinopsins, meridianines, dipodazines and others. g. h. 3. Synthesis of enantiomerically pure functionalized heterocyclic compounds with characteristic structural elements, such as amino acid, peptide, sugar and others. i. j. 4. Regio- in stereoselective 1,3-dipolar cycloadditions of 3-pyrazolinone-1-azomethyne imines to chiral and achiral dipolarophiles. Within this topic will be of especial interest the synthesis of derivatives of 2-amino-7-carboxypyrazolo[1,2-a]pyrazol-1-ones with a dipeptide structural element. k.
Significance for science
This research represents new discoveries in the field of heterocyclic chemistry, especiall on the synthesis of polysubstituted polycarboxylates of 1,3-buatadienes, prepared [2+2]cycloaddition of aminopropenoates to electron-poor acetylene dicarboxylates. Of special significance is the synthesis of new chiral solvating agents on the basis of diketopiperazines, prepared in connction with the synthesis of tryprostatines, neoechinuklines and isoneoechinulines, and their application for determination of enantiomeric purity of aminia acids and their derivatives.
Significance for the country
On national level tis research represents novel knowledge and broadening of the novwel knowledge mostly to diploma and Ph. D. students, who find employment in reseach units of pharmaceutical and chemical industries.
Most important scientific results Annual report 2008, 2009, final report, complete report on dLib.si
Most important socioeconomically and culturally relevant results Annual report 2008, 2009, final report, complete report on dLib.si
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