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METHOD FOR PRODUCING PYRROLIDINE COMPOUND

Provided is a method capable of efficiently producing a compound having a superior HSD1 inhibitory action and a compound useful as a synthetic intermediate therefor, with superior achievability of asymmetric synthesis (i.e., superior selectivity), superio

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Oxazolidine | C3H2620NO – PubChem

 

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Chemistry is an experimental science, and the best way to enjoy it and learn about it is performing experiments. Recommanded Product: 184363-66-4. Introducing a new discovery about 184363-66-4, Name is (S)-4-Phenyl-3-propionyloxazolidin-2-one

Synthesis of the ABCDEFG ring system of maitotoxin

Maitotoxin (1) continues to fascinate scientists not only because of its size and potent neurotoxicity but also due to its molecular architecture. To provide further support for its structure and facilitate fragment-based biological studies, we developed an efficient chemical synthesis of the ABCDEFG segment 3 of maitotoxin. 13C NMR chemical shift comparisons of synthetic 3 with the corresponding values for the same carbons of maitotoxin revealed a close match, providing compelling evidence for the correctness of the originally assigned structure to this polycyclic system of the natural product. The synthetic strategy for the synthesis of 3 relied heavily on our previously developed furan-based technology involving sequential Noyori asymmetric reduction and Achmatowicz rearrangement for the construction of the required tetrahydropyran building blocks, and employed a B-alkyl Suzuki coupling and a Horner-Wadsworth-Emmons olefination to accomplish their assembly and elaboration to the final target molecule.

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A new highly chemoselective isomerization of allylamides

This work describes the first iridium-catalyzed isomerization of N-allylamides into enamides. This strategy allows the chemoselective preparation of (E)-N-(1-propenyl)-enamides and can be applied for the selective deprotection of N-allylamides.

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General Asymmetric Synthetic Strategy for the alpha-Alkylated 2,5,6-Trisubstituted Pyran of Indanomycin and Related Natural Products

A general synthetic strategy for convergent asymmetric synthesis of C1?C10 fragment of tetraene-containing natural product indanomycin was achieved starting from 2-(benzyloxy)acetaldehyde which in turn was obtained from very inexpensive material cis-1,4-butene-diol. Key steps include Evans’ aldol reaction, HWE olefination, iodine-catalyzed tandem isomerization followed by C?O and C?C bond formation similar to our earlier report in constructing the trans-2,6-disubstituted dihydropyran ring and Evans’ asymmetric alkylation.

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Stereoselective Synthesis of Pyrido- and Pyrrolo[1,2-c][1,3]oxazin-1-ones via a Nucleophilic Addition-Cyclization Process of N,O-Acetal with Ynamides

An efficient asymmetric approach to access functionalized pyrido- and pyrrolo[1,2-c][1,3]oxazin-1-ones has been developed through a nucleophilic addition-cyclization process of N,O-acetal with ynamides. A number of substituted ynamides 8a-8o and 3-silyloxypyrrolidine or piperidine N,O-acetals 6a, 7 were amenable to this transformation, and the desired products 9a-9o, 10a-10m were obtained with excellent regioselectivities and outstanding diastereoselectivities. Moreover, chiral ynamides 14a-14f could also experience this addition-cyclization process to afford products 15a-15f in excellent yields.

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Electrogenerated Superoxide-Activated Carbon Dioxide. A New Mild and Safe Approach to Organic Carbamates

The electrochemical reduction of O2 (E = -1.0 V vs SCE) in dipolar aprotic solvents in the presence of CO2 gave a carboxylating reagent (O2¡¤-/CO2) able to convert amines and different types of their derivatives into carbamates. Primary and secondary aliphatic and aromatic amines were converted into the corresponding ethyl carbamates by the addition of EtI to the carbamate anions generated in the first step of the reactions. The yields were dependent on the nucleophilicity of the nitrogen atom omega-Bromoethyl- and propylamine gave 2-oxazolidinone and tetrahydro-l,3-oxazm-2-one in moderate yields. N-Acyl or N-(alkoxycarbonyl)alkylamines bearing a leaving group at the beta position of the alkyl substituent were converted into 3-substituted-2-oxazolidinones in high yields. By using chiral substrates, enantiopure 3-alkoxycarbonyl(or acyl)-4-substituted oxazolidin-2-ones (70-85% isolated yields) were obtained. This represents a new mild and safe route to these important auxiliaries for asymmetric synthesis. Some limitations of the process are also evidenced and accounted for.

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N-Heterocyclic derived M1 positive allosteric modulators

Replacement of a phenyl ring with N-linked heterocycles in a series of quinolone carboxylic acid M1 positive allosteric modulators was investigated. In particular, a pyrazole derivative exhibited improvements in potency, free fraction, and CNS exposure.

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Discovery of potent and novel S-nitrosoglutathione reductase inhibitors devoid of cytochrome P450 activities

The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious S-nitrosoglutathione reductase (GSNOR) inhibitor and is currently undergoing clinical development for the treatment of acute asthma. GSNOR is a member of the alcohol dehydrogenase family (ADH) and regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). Reduced levels of GSNO, as well as other nitrosothiols (SNOs), have been implicated in the pathogenesis of many diseases including those of the respiratory, cardiovascular, and gastrointestinal systems. Preservation of endogenous SNOs through GSNOR inhibition presents a novel therapeutic approach with broad applicability. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogues of N6022 focusing on removal of cytochrome P450 inhibition activities. We identified potent and novel GSNOR inhibitors having reduced CYP inhibition activities and demonstrated efficacy in a mouse ovalbumin (OVA) model of asthma.

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Asymmetric epoxidation of chalcone catalyzed by reusable poly-l-leucine immobilized on hydrotalcite

Nanohybrid materials based on polyamino acids immobilized onto inorganic materials are of interest for their potential applications in protein engineering, biomedicine and catalysis. We developed an efficient and eco-friendly new protocol for the immobilization of synthesized poly-l-leucine (PLL) onto rehydrated hydrotalcite (HTr). To do this, we synthesized different PLLs containing both C-terminal and N-terminal groups and compared them with a commercial PLLc. These synthetic polypeptides were immobilized onto HTr in water as the liquid medium with less than 30 min of ultrasound treatment. The obtained PLLs/HTr synzyme showed excellent activity and enantioselectivity when used as a catalyst in the asymmetric Juli-Colonna epoxidation reaction of chalcone. Moreover, these nanohybrid materials based on PLLS did not require any pre-activation time, which were easily separated from the reaction media and, unlike the commercial PLLc-supported catalyst, were reusable, exhibiting high stability after five consecutive runs without any apparent deactivation.

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A green synthetic route to imides from terminal alkynes and amides by simple solid catalysts

An atom-efficient and green synthetic route to highly valuable imides (5492% yields) from terminal alkynes and amides has been developed. This new route is composed of two consecutive reactions, that is, (i) the reported Cu(OH)2-catalyzed cross-coupling of terminal alkynes and amides to ynamides and (ii) the SnWmixed oxide-catalyzed regioselective hydration of ynamides.

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