55677-61-7Relevant academic research and scientific papers
Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
Sabatini, Marco T.,Karaluka, Valerija,Lanigan, Rachel M.,Boulton, Lee T.,Badland, Matthew,Sheppard, Tom D.
, p. 7033 - 7043 (2018/05/04)
Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.
Total Synthesis of tricladins a and b and identification of their absolute configuration
Zhao, He,Huang, Zhongping,Chen, Wen
, p. 11290 - 11294 (2015/01/08)
A concise synthesis of both (S)- and (R)-enantiomers of tricladins A and B from l-Boc alanine was achieved. The diastereomeric intermediates were separated by chiral column chromatography, and the absolute configuration of the 2-position was assigned by observed NOE interactions with the known stereogenic center at the 5-position. By comparison of all synthesized final enantiomers with the corresponding natural products, we concluded that the natural tricladins A and B must have the (R)-configuration.
