192328-47-5Relevant academic research and scientific papers
Synthesis of orthogonally protected actinoidic acid trimethyl ether
Amino, Yusuke,Williams, Robert M.
, p. 83 - 92 (2019/07/02)
- We describe the asymmetric synthesis of actinoidic acid trimethyl ether with orthogonal protecting groups on the respective amino and carboxyl groups. The Stille biaryl coupling reaction of suitably functionalized aryl bromide and (trimethylstannyl)benz
Racemization in Suzuki couplings: A quantitative study using 4-hydroxyphenylglycine and tyrosine derivatives as probe molecules
Prieto, Monica,Mayor, Silvia,Rodriguez, Katy,Lloyd-Williams, Paul,Giralt, Ernest
, p. 1047 - 1050 (2008/02/04)
(Chemical Equation Presented) Reaction conditions considered to be typical in Suzuki couplings can cause significant (up to 34% of the unwanted enantiomer) loss of optical purity in sensitive substrates such as hydroxyphenylglycine 1. This may be remedied using sodium succinate instead of sodium carbonate as base, but chemical yields are somewhat lower. Optically pure biaryl amino acids related to those found in the chloropeptins and vancomycin were synthesized by Suzuki coupling of 1 with indolylboronic acids 6-8 and with cyclic boronic acid 9.
Synthesis of the vancomycin CD and DE ring systems
Boger, Dale L.,Borzilleri, Robert M.,Nukui, Seiji,Beresis, Richard T.
, p. 4721 - 4736 (2007/10/03)
Full details of the synthesis of the fully substituted vancomycin CD and DE ring systems are described and a potential solution to the control of the atropisomer stereochemistry is defined.
