109579-09-1Relevant articles and documents
An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin
Si, Chang-Mei,Shao, Lu-Ping,Mao, Zhuo-Ya,Zhou, Wen,Wei, Bang-Guo
, p. 649 - 661 (2017)
A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.
Facile synthesis of N-protected γ and δ-amino-β-keto-esters
Li, Baoqing,Franck, Richard W.
, p. 2629 - 2634 (1999)
The C-acylation of Meldrum's acid by protected amino acids, using isopropenyl chloroformate (IPCF) as the condensing agent, is described. The process is used to synthesize γ and δ-amino-β-keto-esters.
4-oxo-alkylated tetramic acid compounds and preparation method thereof
-
, (2017/12/09)
The invention relates to novel compounds and a preparation method thereof. The general structural formula is shown as formula I in the description. Animal experiments prove that the compounds have the effect of saving memories of animal models, are high in safety, have no mutagenicity, can remain in blood for hours after oral administration and intravenous injection, can enter brains and can be used for preparing drugs for treating diseases such as Alzihemer's disease, Parkinson's disease, Huntington's disease, vascular dementia, schizophrenia, autism and the like.
4-oxo-alkylated tetramic acid compound as well as preparation method and application thereof
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, (2018/01/09)
The invention relates to a novel compound as well as preparation method and application thereof. The structural formula of the novel compound is as shown in a formula I. Animal tests show that the compound provided by the invention has a memory effect of rescuing animal models, is high in security and free of mutagenicity induction, can be retained for hours in blood after oral taking and intravenous injection, can be fed into brains and can be used for preparing medicines for treating senile dementia, Parkinsonism, Huntington diseases, vascular dementia, schizophrenia, autism and the like.
Suzuki-Miyaura coupling based enantioselective synthesis of (+)-epi- Clausenamide and the enantiomer of its 3-deoxy analogue
Zhang, Lu,Zhou, Yumei,Yu, Xiaoming
scheme or table, p. 1217 - 1220 (2012/06/18)
The first enantioselective synthesis of two biologically interesting close analogues of clausenamide, namely (+)-epi-clausenamide and (-)-3-deoxy-epi- clausenamide, was reported. Key steps of the synthesis included construction of the chiral pyrrolinone intermediates from d- and l-serine derivatives, introduction of the C4-phenyl by Suzuki-Miyaura coupling and establishment of the C6 configuration by a threo-selective Grignard reaction. Optimization of the key Suzuki-Miyaura coupling reaction was described in detail. Georg Thieme Verlag Stuttgart · New York.
A synthetic approach to diverse 3-acyltetramic acids via O- to C-acyl rearrangement and application to the total synthesis of penicillenol series
Sengoku, Tetsuya,Nagae, Yuta,Ujihara, Yasuaki,Takahashi, Masaki,Yoda, Hidemi
scheme or table, p. 4391 - 4401 (2012/06/18)
For the efficient approach to medicinally important α-branched 3-acyltetramic acids, the key reaction of O- to C- acyl rearrangement using α-amino-acid-derived 4-O-acyltetramic acids was extensively examined in the presence of various metal salts. Use of
Pyrrolinone-pyrrolidine oligomers as universal peptidomimetics
Raghuraman, Arjun,Ko, Eunhwa,Perez, Lisa M.,Ioerger, Thomas R.,Burgess, Kevin
supporting information; experimental part, p. 12350 - 12353 (2011/10/02)
Peptidomimetics 1-3 were prepared from amino acid-derived tetramic acids 7 as the key starting materials. Calculations show that preferred conformations of 1 can align their side-chain vectors with amino acids in common secondary structures more effectively than conformations of 3. A good fit was found for a preferred conformation of 2 (an extended derivative of 1) with a sheet/β-turn/sheet motif.
A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine
Huang, Wei,Ma, Jing-Yi,Yuan, Mu,Xu, Long-Fei,Wei, Bang-Guo
, p. 7829 - 7837 (2011/10/12)
An efficient approach to trans-4-hydroxylpyrrolidine lactams 1 starting from amino acid is described. The utility of this method has been demonstrated in the synthesis of antipsychotic nemonapride 3 and antiangiogenic streptopyrrolidine 4. Compared four s
Dipeptide analogues containing 4-ethoxy-3-pyrrolin-2-ones
Hosseini, Masood,Kringelum, Henriette,Murray, Anthony,Tonder, Janne E.
, p. 2103 - 2106 (2007/10/03)
Pyrrolidine-2,4-diones (1) are naturally occurring analogues of amino acids. We herein present a facile synthesis of N-acylated, O-alkylated pyrrolin-2-ones (2) in high yield and excellent enantiopurity. Molecular mechanics calculations suggest that the r
Hydroxyoxazolidines as alpha-aminoacetaldehye equivalents: novel inhibitors of calpain.
Peet,Kim,Marquart,Angelastro,Nieduzak,White,Friedrich,Flynn,Webster,Vaz,Linnik,Koehl,Mehdi,Bey,Emary,Hwang
, p. 2365 - 2370 (2007/10/03)
The synthesis of [1-[(5-hydroxy-4-(phenylmethyl)-3-oxazolidinyl)carbonyl]-2-ethylpropy lcarbamic acid phenylmethyl ester (2; MDL 104,903), a potent inhibitor of calpain, is described. Synthesis of related compounds, which offer insights into the mechanism of action for 2, are also described, as is an O-acetyl prodrug derivative of 2.
