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Tytuł:
Ostatnie postępy w syntezie alkaloidów tropanowych i pochodnych tropanu
Recent advances in the synthesis of tropane alkaloids and other tropane derivatives
Autorzy:
Sidorowicz, K.
Kropiwnicki, K.
Łaźny, R.
Powiązania:
https://bibliotekanauki.pl/articles/171941.pdf
Data publikacji:
2015
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
synteza
alkaloidy tropanowe
pochodne tropanów
synteza stereoselektywna
synthesis
tropane alkaloids
tropane derivatives
stereoselective synthesis
Opis:
Tropane alkaloids are a long-known class of compounds possessing an 8-azabicyclo[ 3.2.1]octane skeleton. Many tropane alkaloids posses biological activity (anticholinergic, anti-Parkinsonian, hypotensive), and as such had a significant influence on medicine and played a notable role in the development of organic chemistry [1]. The most known representatives of biologically active tropane alkaloids are: cocaine, atropine, scopolamine, ecgonine, and Bao Gong Teng A. A number of natural tropane alkaloids are chiral compounds, whose preparation in optically active forms is still a big challeng [2]. The biological activity of enantiomers often differs depending on their configurations. Alkaloids are a subject of an intensive research: scopus database contains nearly 200 thousand publications with the word „alkaloid”, and almost 4,500 publications with the phrase „tropane alkaloids” (about half of them have appeared in the last ten years). About 55 papers are devoted to stereoselective synthesis of tropane derivatives in 2000-2015. About half of this concernes stereoselective methods. The organic synthesis of alkaloids has a long history and numerous synthetic approaches to the tropane skeleton have been developed, from the classical synthesis of tropinone by Willstätter at the beginning of the XX century, to more recent developments dealing with asymmetric deprotonation of tropinone with chiral lithium amide bases for the enantioselective synthesis of a range of tropanes [3, 4]. Owing to extensiveness of the field, the current review presents the most interesting, from a synthetic point of view, approaches to tropane derivatives and tropane analogues. Most of the methods of synthesis are long (often several steps), time- and recourses-intensive, and often required elaborate and hardly available starting materials. But there are also notable exceptions, based on the asymmetric deprotonation approach; e.g., from the syntheses of cocaine described in this article, the most efficient one was reported by Lee in 2000 [5]. The concise synthesis (6 steps) gave the unnatural enantiomer of cocaine starting from commercially available tropinone in 78% overall yield. This approach allows to obtain both enantiomers and racemate, by changing type of one reactant only. However, most strategies provide only one enantiomer or racemic mixture of an alkaloid. As can be seen, despite of advances in chemicall science, there is no general way to synthesize majority of the representatives of this group of structurally related compounds.
Źródło:
Wiadomości Chemiczne; 2015, 69, 11-12; 1019-1045
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
Tytuł:
Chiralne amidki litu : właściwości i wybrane zastosowania syntetyczne
Chiral lithium amides : properties and selected synthetic applications
Autorzy:
Piwońska, Magdalena
Powiązania:
https://bibliotekanauki.pl/articles/1409982.pdf
Data publikacji:
2021
Wydawca:
Polskie Towarzystwo Chemiczne
Tematy:
chiralność
synteza stereoselektywna
enolan
indukcja asymetryczna
lit
chirality
stereoselective synthesis
enolate
asymmetric induction
lithium
Opis:
Reactions involving carbonyl groups are one of the most important transformations in organic chemistry. The nucleophilic properties of carbonyl compounds, when they are in the form of enolate ions, offer many possibilities for creating new carbon-carbon bonds in reactions with electrophiles. In the case of cyclic ketones, enolate formation can be stereocontrolled by deprotonation with the use of chiral lithium amides. Stereoselective formation of the chiral lithium enolate determines the stereochemistry of the product of the subsequent reaction with the electrophile. The induction of chirality in the reaction of enolate ions with electrophiles can also be achieved by using metals other than lithium, i.e. magnesium. When other alkali metals are used, an organometallic catalyst containing a chiral ligand must be present in the reaction. The presence of particular structural elements allow distinguishing the chiral lithium amides between eight major classes. Due to the high reactivity of lithium enolates, they are often converted into the silyl enol ether. This is done in two ways: internal quench (in situ reaction with TMSCl) or external quench. Due to aggregation of the chiral lithium amides and, thus, a decrease in asymmetric induction, the addition of LiCl is necessary for reactions run in external quench conditions. Although there are known examples of the use of chiral lithium amides in a catalytic amount in the deprotonation of epoxides, there is only one example of using less than stoichiometric amounts of chiral lithium amides in the deprotonation of ketones. There are many reports in the literature on the use of chiral lithium amides in total syntheses. The chiral lithium amides were used to form chiral enol silyl ether intermediates, e.g. in synthesis of chlortetaine or (+)-ibogamine. They are also used to form chiral lithium enolates which reacts directly with electrophiles, e.g. in synthesis of lasonolide A.
Źródło:
Wiadomości Chemiczne; 2021, 75, 5-6; 771-798
0043-5104
2300-0295
Pojawia się w:
Wiadomości Chemiczne
Dostawca treści:
Biblioteka Nauki
Artykuł
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