Total synthesis of eremophilone

McMurry, John E.; Musser, John H.; Ahmad, Mohammed S.; Blaszczak, Larry C.

doi:10.1021/jo00900a031

Cited by 37 publications

(14 citation statements)

References 10 publications

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“…The series of monosubstituted benzenes could be subclassified into three groups according to their regioselectivity (experimental evidence) [14,15] : orto-para (o-p) directing (substituted with electron-releasing groups, ERGs), meta (m-) directing (substituted with electron withdrawing groups) and ipso (i-)directing (where the substituent is the leaving group). Consequently, it is expected that a good theoretical reactivity descriptor can adequately account for this regioselectivity.…”

Section: Resultsmentioning

confidence: 99%

“…[11] Over time, several cases where FMO fails to predict reactivity, for example, electrophilic aromatic substitution reactions have been reported. [12][13][14][15] It has been recognized that the reactivity of these systems is not determined only by the HOMO or LUMO but one or more different orbitals take place in the response to the reagent (under perturbation). [16][17][18] This could be rationalized within the orbital perturbation theory.…”

Section: Introductionmentioning

confidence: 99%

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Proposal of a simple and effective local reactivity descriptor through a topological analysis of an orbital‐weighted fukui function

et al. 2017

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The prediction of reactivity is one of the long-standing objectives of chemistry, contributing to enforce the link between theory and experiment. In particular, the regioselectivity of aromatic molecules has motivated the proposal of different reactivity descriptors based on foundational theories, like Frontier Molecular Orbital (FMO) theory and density functional theory, to predict and rationalize such regioselectivity. This article examines cases where reactivity descriptors, based on FMO theories, are known to have failed, specifically on electrophilic aromatic substitution reactions, through a simple but effective new reactivity model: the Orbital-weighted Fukui function ( fw-(r)) and its topological analysis. Interestingly, this descriptor proves to be effective in adequately predicting regioselectivities where other approximations failed. © 2017 Wiley Periodicals, Inc.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Proposal of a simple and effective local reactivity descriptor through a topological analysis of an orbital‐weighted fukui function

et al. 2017

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“…Impurities N and J could be synthesized from the same starting material (Y101), as shown in Scheme 5. Impurity N was obtained by reaction of Y101 with acetic anhydride in the presence of DMAP in CH 2 Cl 2 at 30°C [17][18][19]. Treatment of impurity N with mCPBA in CH 2 Cl 2 gave impurity J.…”

Section: Impurity Synthesismentioning

confidence: 99%

Process development of clinical anti-HBV drug Y101: identification and synthesis of novel impurities

Liao

An³

et al. 2015

Res Chem Intermed

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Nine novel process impurities of N-[N-benzoyl-O-(2-dimethylaminoethyl)-L-tyrosyl]-L-phenylalaninol (Y101) observed during the laboratory optimization and later during its bulk synthesis are described in this article. The impurities were monitored by HPLC, and their structures were tentatively assigned on the basis of fragmentation patterns in LC-MS/MS and NMR spectroscopies. All of the impurities were synthesized, and their assigned constitutions were confirmed by co-injection in HPLC. In addition to the formation, synthesis, and characterization, the strategy for minimizing these impurities to a level accepted by the International Conference on Harmonisation (ICH) was also described.Electronic supplementary material The online version of this article (

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“…Ethers with comparable polar and hydrogen bonding solubility parameters to lipophilic amines have an outstanding extraction efficiency but also proved somewhat unsuitable, since the ether group is chemically unstable during the subsequent thermal separation, resulting in solvent oxidation and formation of explosive vapor mixtures. A single alkenyl function group has a positive influence on the extraction effect, but the unsaturated carboncarbon bond might cause unexpected reactions such as oligomerization and electrophilic addition [23]. Consequently, alkanes with their high chemical stability were selected for extraction.…”

Section: Selection Of Inert Solvents In a Single-stage Extractormentioning

confidence: 99%

Novel Thermomorphic Biphasic Amine Solvents for CO2 Absorption and Low-Temperature Extractive Regeneration

Zhang

Misch

Tan

et al. 2011

Chem. Eng. Technol.

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The key challenge in amine-based CO 2 capture from flue gases is to reduce the energy consumption required for solvent regeneration. Lipophilic amines exhibit a thermomorphic phase transition upon heating, giving rise to autoextractive behavior, which intensifies desorption at temperatures well below the boiling point of aqueous solutions. The low regeneration temperature of less than 80°C together with the high cyclic CO 2 loading capacity of ∼0.9 mol CO 2 mol absorbent -1 of such thermomorphic biphasic solvent (TBS) systems permit the use of low-value and even waste heat at temperatures below 100°C for desorption. In order to reduce the exergy demands still further, techniques for enhancing CO 2 release using extractive regeneration with inert solvent addition were investigated at temperatures of 40-50°C to permit the use of waste heat at temperatures of ∼70°C or less. The regeneration of 3 M absorbed lipophilic amine solutions with 0.93 mol mol -1 CO 2 loading by using various additional solvents and the evaluation of the extractive performance in multiple-stage crosscurrent and countercurrent configurations indicated the promise of adding certain hydrophobic solvents to enhance the low-temperature regeneration of TBS absorbents.

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Total synthesis of eremophilone

Cited by 37 publications

References 10 publications

Proposal of a simple and effective local reactivity descriptor through a topological analysis of an orbital‐weighted fukui function

Proposal of a simple and effective local reactivity descriptor through a topological analysis of an orbital‐weighted fukui function

Process development of clinical anti-HBV drug Y101: identification and synthesis of novel impurities

Novel Thermomorphic Biphasic Amine Solvents for CO2 Absorption and Low-Temperature Extractive Regeneration

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