199588-89-1Relevant articles and documents
A Unified Approach to Phytosiderophore Natural Products
Kratena, Nicolas,G?kler, Tobias,Maltrovsky, Lara,Oburger, Eva,Stanetty, Christian
supporting information, p. 577 - 580 (2020/11/02)
This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.
Pd/Cu dual catalysis: Highly enantioselective access to α-substituted α-amino acids and α-amino amides
Huo, Xiaohong,Fu, Jingke,He, Xiaobo,Chen, Jianzhong,Xie, Fang,Zhang, Wanbin
, p. 599 - 602 (2018/02/06)
The asymmetric allylation of glycine iminoesters has been accomplished through a synergistic Pd/Cu catalyst system, affording a range of α-substituted α-amino acids in high yields and with excellent enantioselectivities (88 → 99% ee). The introduction of a Cu-P,N-metallocenyl complex-activated glycine iminoester to the chiral palladium-catalyzed allylic allylation process is crucial owing to its high reactivity and excellent enantioselectivities. Importantly, this Pd/Cu dual catalysis strategy can be used for the asymmetric allylic alkylation of prochiral glycine amide derivatives, which could be further utilized to synthesize biologically important vicinal diamines.
Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates
Vulovic, Bojan,Gruden-Pavlovic, Maja,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 34 - 37 (2014/01/23)
Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.
