91028-46-5Relevant academic research and scientific papers
Catalytic enantioselective synthesis of 4-vinyl-2-trichloromethyloxazoline: An access to enantioenriched vinylglycinol surrogate
Maleckis, Ansis,Klimovica, Kristine,Jirgensons, Aigars
, p. 7897 - 7900 (2010)
Cationic Pd(II) catalysts generated from chiral biphenyl diphosphine complexes or from COP-Cl promote enantioselective cyclization of E- and Z-configured allylic bis-trichloroacetimidates to highly enantioenriched 2-trichloromethyl-4-vinyloxazoline. This
Total Synthesis and Structural Reassignment of Aspergillomarasmine A
Liao, Daohong,Yang, Shaoqiang,Wang, Jianyu,Zhang, Jian,Hong, Benke,Wu, Fan,Lei, Xiaoguang
, p. 4291 - 4295 (2016/04/01)
The increase and spread of Gram-negative bacteria that resistant are to almost all currently available β-lactam antibiotics is a major global health problem. The primary cause for drug resistance is the acquisition of metallo-β-lactamases such as metallo-β-lactamase-1 (NDM-1). The fungal natural product aspergillomarasmine A (AMA), a fungal natural product, is an inhibitor of NDM-1 and has shown promising in vivo therapeutic potential in a mouse model infected with NDM-1-expressing Gram-negative bacteria. The first total synthesis and stereochemical configuration reassignment of aspergillomarasmine A is reported. The synthesis highlights a flexible route and an effective strategy to achieve the required oxidation state at a late stage. This modular route is amenable to the efficient preparation of analogues for the development of metallo-β-lactamase inhibitors to potentiate β-lactam antibiotics.
An efficient and scalable synthesis of N-(benzyloxycarbonyl)- and N-(methyloxycarbonyl)-(S)-vinylglycinol
Lumbroso, Alexandre,Coeffard, Vincent,Le Grognec, Erwan,Beaudet, Isabelle,Quintard, Jean-Paul
supporting information; experimental part, p. 3226 - 3228 (2010/08/19)
An efficient and scalable synthesis of N-(benzyloxycarbonyl)- and N-(methyloxycarbonyl)-(S)-vinylglycinol has been reported starting from the commercially available (l)-methionine. The scale-up preparation consisted of 5 steps and delivered up to 50 g of the desired N-protected β-amino alcohols in 32% and 36% overall yields.
Enantiospecific synthesis of (+)-hyacinthacine A2
Dewi-Wülfing, Purnama,Blechert, Siegfried
, p. 1852 - 1856 (2007/10/03)
We report an efficient synthesis of (+)-hyacinthacine A2 in six steps from (S)-N-Cbz-vinylgylcine. The key strategies were the olefin cross metathesis (CM), Sharpless asymmetric dihydroxylation, and a sequential double reductive cyclization. Wi
SYNTHESIS OF CHROMANONES
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Page 51, (2008/06/13)
Processes for the preparation of biologically active chromanones are disclosed, including processes for the preparation of intermediates useful in the preparation of the biologically active chromanones. The chromanones and the intermediates disclosed herein may be useful for a variety of therapies, including the treatment of various cancers and the treatment of inflammation and inflammation related disorders.
Dynamic kinetic asymmetric transformation of diene monoepoxides: A practical asymmetric synthesis of vinylglycinol, vigabatrin, and ethambutol
Trost, Barry M.,Bunt, Richard C.,Lemoine, Remy C.,Calkins, Trevor L.
, p. 5968 - 5976 (2007/10/03)
The ability to perform a dynamic kinetic asymmetric transformation (DYKAT) using the palladium-catalyzed asymmetric allylic alkylation (AAA) is explored in the context of butadiene monoepoxide. The versatility of this commercially available, but racemic, four-carbon building block becomes significantly enhanced via conversion of both enantiomers into a single enantiomeric product. The concept is explored in the context of a synthesis of vinylglycinol with phthalimide as the nitrogen source. The success of the project required a new design of the ligand for palladium wherein additional conformational restraints were introduced. Thus, the phthalimide derivative of vinylglycinol was obtained in nearly quantitative yield and had an ee of 98% which, upon crystallization, was enhanced to > 99%. This one-step synthesis of a protected form of vinylglycinol provided short practical syntheses of the title compounds. Vigabatrin requires only four steps, and ethambutol six. The intermediate to the existing synthesis of ethambutol is available in 87% yield in three steps. (R)-Serine derives from oxidative cleavage of the double bond. The reaction of phthalimide and isoprene monoepoxide demonstrates the remarkable ability of the chiral ligands to control both regioselectivity and enantioselectivity and demonstrates the effectiveness of this protocol in creating a quaternary center asymmetrically.
Synthesis of unnatural amino acids via suzuki cross-coupling of enantiopure vinyloxazolidine derivatives
Sabat, Mark,Johnson, Carl R.
, p. 1089 - 1091 (2007/10/03)
(R and S)-α-Amino alcohols and α-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant α-amino alcohols are described.
Design von Liganden fuer katalytische Outer-sphere-Reaktionen: eine einfache asymmetrische Synthese von Vinylglycinol
Trost, Barry M.,Bunt, Richard C.
, p. 70 - 73 (2007/10/03)
Keywords: Allylische Alkylierung; Asymmetrische Induktion; Deracemisierung; Katalyse; Uebergangsmetallverbindungen
A Total Synthesis of (-)-α-Kainic Acid By the Pauson-Khand Reaction
Yoo, Sung-eun,Lee, Sang-Hee,Jeong, Nakcheol,Cho, Inho
, p. 3435 - 3438 (2007/10/02)
A total synthetic route to (-)-α-kainic acid has been developed based on the Pauson-Khand reaction as a key reaction for the construction of the bicyclo ring system.
Palladium-catalyzed heck couplings of L-vinylglycine derivatives with vinyl and aryl halides and triflates
Crisp, Geoffrey T.,Glink, Peter T.
, p. 3541 - 3556 (2007/10/02)
The coupling of aryl and vinyl halides and triflates with L-vinylglycine derivatives under the influence of a palladium catalyst is described. The coupling is regioselective and stereoselective with the absolute configuration of the α-amino acid centre be
