3646-50-2Relevant articles and documents
Microwave-assisted synthesis of taxol side-chain precursor from malonic acid
Ehsan,Khan,Ara
, p. 2929 - 2930 (2013)
Being a complex diterpenoid, the potent anticancer drug, taxol requires complicated multistep for its synthesis. Due to the chemical complexity of taxol, its commercial production by total synthesis is not likely to be economical. Another natural product, 10-deacetyl baccatin 111 is readily available in higher yield. Several methods have been reported for the synthesis of taxol by coupling baccatin 111 and the N-benzoyl-β-phenyl isoserine side chain. In this study, a simple precursor of side chain has been synthesized under microwave radiation by the condensation of benzaldehyde, ammonium acetate and malonic acid. The time required for the resulting β-amino acid was remarkably reduced from 6 h to 30 s only along with rapid, easy, simple and safe methodology. The structure elucidation of synthesized compound was done by its melting point, solubility, TLC techniques and spectral analyses.
The kinetic resolution of oxazinones by alcoholysis: access to orthogonally protected β-amino acids
Connon, Stephen J.,Cronin, Sarah A.
supporting information, p. 7348 - 7352 (2021/09/07)
The catalytic, alcoholytic kinetic resolution of oxazinones is reported. A novel, stereochemically dense cinchona alkaloid-based catalyst can facilitate the highly enantiodiscriminatory (Sup to 101) ring-opening of oxazinones equipped with electrophilic aryl units to generate orthogonally protected β-amino acids for the first time.
Base-induced Sommelet–Hauser rearrangement of N-(α-(2-oxyethyl)branched)benzylic glycine ester-derived ammonium salts via a chelated intermediate
Baba, Souya,Hirano, Kazuki,Tayama, Eiji
supporting information, (2020/03/13)
The base-induced Sommelet–Hauser (S–H) rearrangement of N-(α-branched)benzylic glycine ester-derived ammonium salts 1 was investigated. When the α-branched substituent was a simple alkyl, such as a methyl or butyl, desired S–H rearrangement product 2 was obtained in low yield with formation of the [1,2] Stevens rearranged 4 and Hofmann eliminated products 5 and 6. However, when the α-branched substituent had a 2-oxy moiety, such as 2-acetoxyethyl or 2-benzoyloxyethyl, the yields of 2 were improved. These results could be explained by formation of chelated intermediate C that stabilizes the carbanionic ylide, and the subsequent initial dearomative [2,3] sigmatropic rearrangement would be accelerated. The existence of C was supported by mechanistic experiments. This enhancement effect is not very strong or effective; however, it will expand the synthetic usefulness of ammonium ylide rearrangements.