- Tytuł:
-
Synteza γ-laktonów z podstawnikami aromatycznymi
Synthesis of γ-lactones with aromatic substituents - Autorzy:
-
Skrobiszewski, A.
Gładkowski, W. - Powiązania:
- https://bibliotekanauki.pl/articles/171624.pdf
- Data publikacji:
- 2013
- Wydawca:
- Polskie Towarzystwo Chemiczne
- Tematy:
-
gamma laktony
pierścienie aromatyczne
reakcja Suzuki-Miyaury
enzymatyczna estryfikacja i hydroliza
mikrobiologiczna redukcja grupy karbonylowej
diastereoselektywne alkilowanie
enancjoselektywne uwodornienie podwójnego wiązania
gamma-lactones
aromatic rings
Suzuki-Miyaura reaction
enzymatic hydrolysis and acetylation
microbial reduction of a carbonyl group diastereoselective alkylation
enantioselective hydrogenation of olefinic substrates - Opis:
- Biological activities of lactones are predominantly determined by different substituents on a lactone ring. γ-Lactones with aromatic substituents have interesting biological activities and serve as useful intermediates in the synthesis of many natural and synthetic products. Pulvinic and vulpinic acids exhibit antimicrobial, antioxidant and anticancer activity [1–3]. Paraconic acids have anticancer and antibacterial activity [4, 5]. The interesting biological activities i.a. antileukemic, anti- HIV and cytostatic, have been found for dibenzyl-γ-lactones [8]. This review covers some examples of synthetic and biotechnological methods leading to either racemic or optically active γ-lactones with aromatic substituents. The racemic α-benzylidene lactones can be produced from Baylis-Hillman acetates [9]. The multicomponent synthesis of the paraconic acid analogs is performed by a fourfold metallation-conjugate addition-aldol addition-intramolecular transesterification sequence [4]. Suzuki-Miyaura reaction is the key step in the synthesis of asymmetric pulvinic acids [1]. Some other examples of synthetic strategies involving the reactivity of ylides, vicinal dianions, ozonolysis or Claisen rearrangement are also presented [10–13]. Production of optically active γ-lactones with aromatic substituents involves application of biotechnological and chemical methods. The first one includes using commercially available enzymes [16, 17] or whole cells of microorganisms [18–20]. Chemical methods involve application of chiral starting materials like malic acid esters or the derivatives of succinic acid [14, 15] or chiral catalysts like BINAP-Rh or Ru complexes [7].
- Źródło:
-
Wiadomości Chemiczne; 2013, 67, 9-10; 943-960
0043-5104
2300-0295 - Pojawia się w:
- Wiadomości Chemiczne
- Dostawca treści:
- Biblioteka Nauki
Artykuł