2051-96-9Relevant articles and documents
A Short Synthesis of the Mould Metabolite (R)-(+)-Carolinic Acid from (S)-Lactic Acid
Linder, David,Schobert, Rainer
, p. 4564 - 4568 (2016)
(R)-(+)-Carolinic acid was prepared in seven steps and 59% yield from inexpensive benzyl l-lactate, the configuration of which was inverted by a Mitsunobu reaction with trifluoroacetate. The resulting benzyl d-lactate was cyclised by a domino addition-Wittig alkenation reaction with Ph3PCCO. The product tetronic acid was acylated with a second equivalent of this ylide to give a 3-acylylidenetetronic acid, which was olefinated directly with tert-butyl glyoxylate. The product alkene was hydrogenated and deprotected to afford pure crystalline (R)-(+)-carolinic acid, which proved inactive against Staphylococcus aureus and Escherichia coli mutant D21f2.
Organocatalytic chain scission of poly(lactides): A general route to controlled molecular weight, functionality and macromolecular architecture
Nederberg,Connor,Glausser,Hedrick
, p. 2066 - 2067 (2001)
A facile, single-step transesterification approach to poly(lactides) with controlled molecular weights and end-group functionality, as well as block and star-shaped architectures is described using nucleophilic amine catalysts.
A NEW TEMPLATE of MITSUNOBU ACYLATE CLEAVABLE in NONALKALINE CONDITIONS
Sai, Yusuke,Sakakibara, Yoshimichi,Shigetomi, Kengo,Ubukata, Makoto,Uraki, Yasumitsu
, p. 140 - 158 (2022/01/08)
The Mitsunobu inversion is one of the reliable methods for stereospecific substitution of chiral alcohols, but its deacylation step has limited the substrate scope. Here, we propose a new template of the Mitsunobu acylate that can be deacylated in non-alkaline treatments. The 3,4-dihydroxy-2-methylenebutanoate was selected as a template structure, and its acetonide- or bisTBS derivatives were synthesized. The latter especially showed excellent inversion efficiency (up to >99% ee) and good elimination performance for a series of secondary alcohols in near-neutral conditions. The results demonstrated the applicability of the new template for the substrates labile in alkaline conditions, such as a-hydroxyesters.
Functional Models of the Nickel Pincer Nucleotide Cofactor of Lactate Racemase
Shi, Renyi,Wodrich, Matthew D.,Pan, Hui-Jie,Tirani, Farzaneh Fadaei,Hu, Xile
supporting information, p. 16869 - 16872 (2019/11/13)
A novel nickel pincer cofactor was recently discovered in lactate racemase. Reported here are three synthetic nickel pincer complexes that are both structural and functional models of the pincer cofactor in lactate racemase. DFT computations suggest the ipso-carbon atom of the pyridinium pincer ligands act as a hydride acceptor for lactate isomerization, whereas an organometallic pathway involving nickel-mediated β-hydride elimination is less favored.