Repozytorium
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Kolekcje
Inne
Alkaloids as Chiral Building Blocks, Auxiliaries, Ligands, and Molecular Diversity
Autorzy
Rok wydania
2022
Wydawca
Wiley-VCH
Miejsce wydania
Weinheim
Strony
297-366
DOI
10.1002/9783527834204.ch10
Tytuł książki
Chiral Building Blocks in Asymmetric Synthesis : Synthesis and Applications
ISBN
978-3-527-34946-3
Kolekcja
Język
Angielski
Typ publikacji
Rozdział książki
Among c. 20 000 of known alkaloids isolated from natural sources and their numerous derivatives, few belong to privileged chiral molecules that shaped the stereochemistry and enantioselective synthesis since their birth. Alkaloids, initially used as efficient resolving agents, currently provide a rich portfolio of powerful chiral ligands, organocatalysts, and to lesser extent auxiliaries dedicated to CC and C–heteroatom bond formation. These include ephedra, lupine, and Cinchona alkaloids and their derivatives. The biological activity of alkaloids makes them suitable to target biologically relevant chemical space by providing chiral, medicinally favored scaffolds for preparation of diversity-oriented libraries. Recently, even structurally complex alkaloids have been demonstrated to be a valuable source for generating chiral molecular diversity by ring-distortion approach. Alkaloids with a combination of novel synthetic tools comprising cross-coupling chemistry, CH-heteroarene functionalization, or click chemistry provide an access to libraries for catalytic and biological screening. Problems with availability of the alkaloids as well as restriction regarding the use of many of them make the development of alkaloid chemistry slower than it deserves.