Atroposelektywna synteza naturalnych chiralnych osiowo związków biarylowych. Część 2
Journal Title: Wiadomości Chemiczne - Year 2017, Vol 71, Issue 3
Abstract
A direct aryl-aryl coupling reaction is the most common method for the synthesis of axially chiral biaryls. Atroposelective coupling can be accomplished by three main strategies (Scheme 1) [1, 11]: a) intramolecular coupling reaction between two aryl substrates by the use of the chiral tether as a source of asymmetric information (Scheme 2), b) intermolecular reaction of the modified aryl compounds containing a chiral auxiliary. A source of chiral information can be a planar-chiral element, the chiral leaving group, and the chiral ortho substituent (Scheme 12, 16, 17), c) intermolecular coupling in the presence of chiral additives, for example, stoichiometric or catalytic oxidation in the presence of the transition metal complexes containing chiral ligands, and the redox-neutral coupling reactions catalyzed by transition metal complexes with chiral bidentate N/P- -ligands (Scheme 18, 20–22). These methods have been applied in the synthesis of various biologically active compounds. For example, Lipshutzet et al. obtained a fragment of the antibiotic vancomycin [15], and O-permethyltellimagrandin II [16]. Lin and coworkers synthesized (P)-kotanin [17], the natural metabolite from Aspergillus glaucus (Scheme 3). Waldvogel and coworkers [19] received steganacin derivative, a cytostatic drug (Scheme 5). Coleman et al. in the oxidative dimerization reaction of aryls with a chiral ortho substituents obtained a precursor in the synthesis of calphostin A (Scheme 8) [26]. Meyers and coworkers [27, 28] applied the Ullmann homocoupling for the synthesis of gossypol (Scheme 9). The oxidative coupling of phenols allows to obtain the natural precursor of nigerone (Scheme 13) [42]. Whereas the calphostin [18] derivative, an inhibitor of protein kinase C, was obtained by the oxidative coupling reaction (Scheme 4). The schizandrin [23] from Schisandra chinensis and isodiospyrin [24] from Diospyros morrisiana were obtained by intermolecular coupling reaction of aryl substrates with the chiral ortho substituents (Scheme 7).
Authors and Affiliations
Renata Kołodziejska, Agnieszka Tafelska-Kaczmarek
Keywords
Related Articles
- EP ID EP568479
- DOI -
- Views 140
- Downloads 0
Fotoaktywne układy polimerowe o rozmiarach nanometrycznych
Sun is the most powerful source of clean, cheap and environmentally friendly source of energy, but still, the usage of this resource cover less than 1% of current world energy requirements [1]. However, nature realizes e...
Jubileusz metody miareczkowania kulometrycznego
In 1938, Szebellédy and Somogyi [1–7] have proposed an important methodological innovation in analytical chemistry. This methodology was termed coulometric titration. This paper presents an overview of the principles of...
Enancjoselektywna enzymatyczna desymetryzacja katalizowana lipazami. Część II, Optymalizacja warunków reakcji. Związki mezo
In the enzymatic asymmetric synthesis, the enzyme allows the desymmetrization of achiral compounds resulting in chiral compounds of high optical purity. Meso compounds (bearing a plane of symmetry) are very important gro...
Wpływ warunków parzenia na zawartość antyoksydantow w naparach różnych rodzajów herbat
Tea has been consumed all over the World for over two thousand years and now it is the most popular caffeine-containing beverage. Its worldwide consumption is second only to water [1–3]. The tea is not only important bec...
Krytyczne stężenie micelarne i metody jego wyznaczania
Surfactants are substances, which have surface activity in aqueous solutions [1–3]. By adsorbing on the surface (boundary of phase separation) of the system, they change the surfactant properties of the liquid. Surfactan...