Where is the Oxygen? Structural Analysis of α‐Humulene Oxidation Products by the Crystalline Sponge Method

Zigon, Nicolas; Hoshino, Manabu; Yoshioka, Shin; Inokuma, Yasuhide; Fujita, Makoto

doi:10.1002/anie.201502302

Cited by 77 publications

(45 citation statements)

References 29 publications

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“…By soaking guests into porous coordination networks (crystalline sponges), the guests are oriented for SCD study 4. For the practical use of this method, a detailed protocol5 and experimental guidelines6 have been reported.…”

Section: Introductionmentioning

confidence: 99%

Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method

et al. 2015

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Section: Introductionmentioning

confidence: 99%

Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method

et al. 2015

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“…[15] Ar ecently reported study indicated that retrocycloisomerization of (À)-caryophyllene oxide by catalysis using Jacobsen's cobalt(II) salen complex yields (À)-humulene oxide II (humulene 6,7-epoxide). Despite some reports on its synthesis, obtaining humulene diepoxide (1)e nantioselectivelyi sd ifficult.…”

Section: Resultsmentioning

confidence: 99%

Development of a Terpenoid Alkaloid‐like Compound Library Based on the Humulene Skeleton

Kikuchi

Nishimura

Kwon

et al. 2016

Chemistry A European J

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Many natural terpenoid alkaloid conjugates show biological activity because their structures contain both sp -rich terpenoid scaffolds and nitrogen-containing alkaloid scaffolds. However, their biosynthesis utilizes a limited set of compounds as sources of the terpenoid moiety. The production of terpenoid alkaloids containing various types of terpenoid moiety may provide useful, chemically diverse compound libraries for drug discovery. Herein, we report the construction of a library of terpenoid alkaloid-like compounds based on Lewis-acid-catalyzed transannulation of humulene diepoxide and subsequent sequential olefin metathesis. Cheminformatic analysis quantitatively showed that the synthesized terpenoid alkaloid-like compound library has a high level of three-dimensional-shape diversity. Extensive pharmacological screening of the library has led to the identification of promising compounds for the development of antihypolipidemic drugs. Therefore, the synthesis of terpenoid alkaloid-like compound libraries based on humulene is well suited to drug discovery. Synthesis of terpenoid alkaloid-like compounds based on several natural terpenoids is an effective strategy for producing chemically diverse libraries.

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“…However, the potential to inspect unstable moieties or molecules that are not easily crystallised in pure form is highly attractive, and a range of targets has been recently investigated to further demonstrate the utility of the strategy. [54][55][56][57][58][59][60][61] The characterised guest molecules range from simple molecules 54 to reactive acrylate esters 56 and complex Please do not adjust margins Please do not adjust margins molecules with axial and planar chirality, 58 (1R)-(-)-menthyl acetate, 59 α-humulene and its oxidized subproducts. 60 The 'crystalline sponge' approach has also been developed for porous organic materials 61 mirroring studies in MOFs.…”

Section: Mof As Crystallisation Matricesmentioning

confidence: 99%

Emerging applications of metal–organic frameworks

et al. 2016

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Metal-organic Frameworks are a unique class of materials well known for their crystallinity and ultra-high porosity. Since their first report over fifteen years ago, research in this area has sought to actively exploit these properties, especially in gas adsorption. In this article we canvass some emerging topics in the field of MOF research that show promise for new applications in areas such as biotechnology, catalysis, and microelectronics. 26 and Cytochrome c 27 into Tb-based MOFs. These examples were limited to biomacromolecules with sizes smaller than the MOF cavities, although more recent work by Yaghi and coworkers 28has demonstrated the precise tuning of the pore size to adsorb and accommodate bigger biomacromolecules, such as myoglobin and green fluorescent protein.

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Where is the Oxygen? Structural Analysis of α‐Humulene Oxidation Products by the Crystalline Sponge Method

Cited by 77 publications

References 29 publications

Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method

Absolute structure determination of compounds with axial and planar chirality using the crystalline sponge method

Development of a Terpenoid Alkaloid‐like Compound Library Based on the Humulene Skeleton

Emerging applications of metal–organic frameworks

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