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Asymmetric total synthesis of (+)-didemniserinolipid b via achmatowicz rearrangement/bicycloketalization

A new synthetic strategy was developed for the asymmetric total synthesis of (+)-didemniserinolipid B in 19 linear steps, featuring a highly efficient and enantioselective construction of 6,8-dioxabicyclo[3.2.1]octane (6,8-DOBCO) framework via a rarely explored Achmatowicz rearrangement/bicycloketalization strategy. In addition, the first total synthesis of the proposed (+)-didemniserinolipid C was accomplished with 41.6% yield in 4 steps from a common advanced intermediate 18, and a possible revised structure of (+)-didemniserinolipid C was proposed. The new convergent synthetic strategy greatly expedites the entry to the didemniserinolipids and their analogues for biological activity evaluation.

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More research is needed about 122433-29-8

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Transformation of d-serine to highly functionalized cyclohexenecarboxylates in study of oseltamivir synthesis

In an attempted synthesis of oseltamivir, D-serine was used to prepare (R)-Garner aldehyde, which reacted with vinylzinc reagent to give an alcohol product predominating in the (1?R,4S)-isomer. After the alcohol was protected as p-methoxybenzyl ether, the N,O-acetal was hydrolyzed and oxidized to an aldehyde, which underwent Reformatsky-type reaction with ethyl alpha-(bromomethyl)acrylate by promotion of indium to give an addition product readily for ring-closure metathesis to afford 3-alkoxy-4-amido-5-hydroxy-1- cyclohexenecarboxylates. After activation of the 5-hydroxy group as methanesulfonate, an attempted substitution reaction with sodium azide gave unexpectedly a cyclic carbamate via an intramolecular nucleophilic attack of the 4-tert-butoxycarbamate group.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents

Alcohols undergo smooth oxidation with iodoxybenzoic acid (IBX) or with Dess-Martin-Periodinane (DMP) in hydrophilic [bmim]BF4 and hydrophobic [bmim]PF6 ionic liquids at room temperature under mild conditions to afford the corresponding carbonyl compounds in excellent yields with high selectivity. IBX and DMP promoted oxidations are faster in ionic liquids when compared to conventional solvents such as DMSO, DMF, EtOAc and H2O. The recovery of the byproduct iodosobenzoic acid (IBA) is especially simple in ionic liquids. The recovered ionic liquids can be recycled in subsequent reactions with consistent activity.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The important role of 1-(Benzo[d]oxazol-2-yl)ethanone

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Metal-mediated alkynediol cycloisomerization: First and second generation formal total syntheses of didemniserinolipid B

A formal total synthesis of didemniserinolipid B was developed by employing a regioselective metal-mediated 6-endo-dig alkynol-cycloisomerization reaction. Two routes for the synthesis of key Burke’s intermediate have been developed. Our initial approach involved the introduction of a C17-alkynol followed by Pd-mediated cycloisomerization and then coupling with the serinol unit prior to the introduction of an alpha,beta-unsaturated ester unit through selective oxidation of 1-OH followed by a two-carbon Wittig homologation. Alternatively, the second generation strategy featuring the serinol coupling with the C17-alkynol followed by alkyne addition to the epoxide and subsequent Au-mediated cycloisomerization of an acetonide protected alkynediol unit has been executed. This approach has avoided several late stage protection-deprotection events.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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New Antibiotic Candidates against Helicobacter pylori

Helicobacter pylori is a Gram-negative bacterium that colonizes the gut of over 50% of the worlds population. It is responsible for most peptic ulcers and is an important risk factor for gastric cancer. Antibiotic treatment for H. pylori infections is challenging as drug resistance has developed to antibiotics with traditional mechanisms of action. H. pylori uses an unusual pathway for menaquinone biosynthesis with 5?-methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTAN) catalyzing an essential step. We validated MTAN as a target with a transition-state analogue of the enzyme [Wang, S.; Haapalainen, A. M.; Yan, F.; et al. Biochemistry 2012, 51, 6892-6894]. MTAN inhibitors will only be useful drug candidates if they can both include tight binding to the MTAN target and have the ability to penetrate the complex cell membrane found in Gram-negative H. pylori. Here we explore structural scaffolds for MTAN inhibition and for growth inhibition of cultured H. pylori. Sixteen analogues reported here are transition-state analogues of H. pylori MTAN with dissociation constants of 50 pM or below. Ten of these prevent growth of the H. pylori with IC90 values below 0.01 mug/mL. These remarkable compounds meet the criteria for potent inhibition and cell penetration. As a consequence, 10 new H. pylori antibiotic candidates are identified, all of which prevent H. pylori growth at concentrations 16-2000-fold lower than the five antibiotics, amoxicillin, metronidazole, levofloxacin, tetracyclin, and clarithromycin, commonly used to treat H. pylori infections. X-ray crystal structures of MTAN cocrystallized with several inhibitors show them to bind in the active site making interactions consistent with transition-state analogues.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Regioselective cleavage of the bis-benzylidene acetal of D-mannitol under oxidative and reductive conditions: A new approach to C2-symmetric chiral ligands

A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was carried out using NBS and the resultant product was readily converted to the C2-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5- hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was achieved in a highly regioselective manner using BF 3?OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C2-symmetric bis-amino alcohol derivative.

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Benzoxazole – Wikipedia,
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Extracurricular laboratory:new discovery of 1-(Benzo[d]oxazol-2-yl)ethanone

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Optimization of 1H-tetrazole-1-alkanenitriles as potent orally bioavailable growth hormone secretagogues

1H-Tetrazole-1-alkanenitrile SR-9g exhibits a >10-fold in vivo potency enhancement over the lead nitrile 1 and has acceptable oral bioavailability in rats and dogs. An enantiospecific synthesis of 1H-tetrazole-1-alkanenitrile nitriles 9 has been developed.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Simple exploration of 1-(Benzo[d]oxazol-2-yl)ethanone

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Synthesis of (+)-didemniserinolipid B: Application of a 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis

(Chemical Equation Presented) The synthesis of didemniserinolipid B utilizing a ketalization/ring-closing metathesis (K/RCM) strategy is described. In the course of this work, a novel 2-allyl-4-fluorophenyl auxiliary for relay ring-closing metathesis (RRCM) was developed, which increased the yield of the RCM. The resulting 6,8-dioxabicyclo[3.2.1]octene core was selectively functionalized by complimentary dihydroxylation and epoxidation routes to install the C10 axial alcohol. This bicyclic ketal core was further functionalized by etherification and an alkene cross metathesis with an unsaturated a-phenylselenyl ester en route to completing the total synthesis.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Synthesis of N-(tert-butoxycarbonyl)-N,O-isopropylidene serinal from serine methyl ester by a reduction-oxidation sequence

The title aldehyde is prepared by LiAlH4 reduction of the corresponding serine derived methyl ester to the alcohol and Swern oxidation of the latter. The aldehyde is obtained in 94 % yield and 96-98 % enantiomeric purity. This method avoids some problems encountered in the synthesis of the same aldehyde by direct controlled DIBAL reduction of the ester.

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Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

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Application of 122433-29-8, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Patent, and a compound is mentioned, 122433-29-8, 1-(Benzo[d]oxazol-2-yl)ethanone, introducing its new discovery.

4,5-DIHYDRO-OXAZOL-2YL DERIVATIVES

The invention relates to compounds of formula I wherein R1, R2, X, Y, and n are defined in the specification and to pharmaceutically acceptable acid addition salts thereof. The invention also provides pharmaceutical compositions and methods of manufacture of such compounds. The compounds are useful for the treatment of diseases related to the biological function of the trace amine associated receptors, which diseases are depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders, schizophrenia, neurological diseases, Parkinson’s disease, neurodegenerative disorders, Alzheimer’s disease, epilepsy, migraine, substance abuse and metabolic disorders, eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders

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Reference£º
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem