Academic literature on the topic 'Ophiorrhiside E'

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Journal articles on the topic "Ophiorrhiside E"

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Kitajima, Mariko, Tadayoshi Onozawa, Noriyuki Kogure, and Hiromitsu Takayama. "Elucidation of Absolute Configuration of Ophiorrhiside A by Comparison of ECD Spectra with That of Model Chiral Compound Having a 1,2,3,4-Tetrahydro-β-Carbolin-3-one Skeleton." HETEROCYCLES 102, no. 1 (2021): 35. http://dx.doi.org/10.3987/com-20-14351.

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Onozawa, Tadayoshi, Mariko Kitajima, Noriyuki Kogure, and Hiromitsu Takayama. "Asymmetric Total Synthesis and Evaluation of Antitumor Activity of Ophiorrhisine A and Its Derivatives." Journal of Organic Chemistry 83, no. 24 (November 19, 2018): 15312–22. http://dx.doi.org/10.1021/acs.joc.8b02554.

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3

Cao, Wei, Yingchao Dou, Cyrille Kouklovsky, and Guillaume Vincent. "Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels‐Alder Cycloaddition." Angewandte Chemie, July 22, 2022. http://dx.doi.org/10.1002/ange.202209135.

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4

Cao, Wei, Yingchao Dou, Cyrille Kouklovsky, and Guillaume Vincent. "Total Synthesis of Ophiorrhine A, G and Ophiorrhiside E Featuring a Bioinspired Intramolecular Diels‐Alder Cycloaddition." Angewandte Chemie International Edition, July 22, 2022. http://dx.doi.org/10.1002/anie.202209135.

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Dissertations / Theses on the topic "Ophiorrhiside E"

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Cao, Wei. "Total synthesis of ophiorrhine A, G and ophiorrhiside E and synthetic studies towards the total synthesis of pestalustaine A." Electronic Thesis or Diss., université Paris-Saclay, 2024. http://www.theses.fr/2024UPASF077.

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Abstract:
L'ophiorrhine A, G et l'ophiorrhiside E sont des alcaloïdes indolomonoterpéniques isolés des plantes Ophiorrhiza japonica et Trichocarpon. Nous avons réalisé la première synthèse totale de l'ophiorrhine A, G et de l'ophiorrhiside E. Plusieurs stratégies ont été explorées pour construire la partie indolopyridone de l'ophiorrhiside E, le précurseur biosynthétique supposé de l'ophiorrhine A. Finalement, le couplage de type Friedel-Crafts de l'indolyl-acétamide avec le chlorure d'acide dérivé de la sécologanine a conduit à l'ophiorrhine G. La cyclodéshydratation d'une forme protégée de ce dernier a été suivie par la cycloaddition de Diels-Alder intramoléculaire spontanée de l'ophiorrhiside E protégée, menant à l'ophiorrhine A, qui peut se transformer en un produit non naturel avec un squelette de carbazole. La pestalustaïne A est un sesquiterpénoïde isolé du champignon endophyte pestalotiopsis adusta dont nous avons investigué la synthèse totale. Nous avons réalisé une expansion de cycle à partir d'un intermédiaire à 6 chaînons pour former un noyau à 7 chaînons, suivie par une fermeture de cycle par métathèse d'un diène pour construire un squelette ponté 7/7, et une addition 1,4 intramoléculaire pour obtenir le tricycle 7/5/6. L'analyse des résultats de diffraction des rayons X pour un intermédiaire contenant le noyau 7/5/6 a révélé des écarts entre notre structure et celle proposée précédemment. L'analyse des spectres du produit naturel isolé a suggéré que la structure avait peut-être été mal attribuée
Ophiorrhine A, G and ophiorrhiside E are monoterpene indole alkaloids which were isolated from the plant Ophiorrhiza japonica and trichocarpon. We achieved the first total synthesis of ophiorrhine A, G and ophiorrhiside E. Several strategies were investigated to construct the indolopyridone moiety of ophiorrhiside E, the postulated biosynthetic precursor of ophiorrhine A. Eventually, the Friedel-Crafts-type coupling of indolyl-acetamide with secologanin-derived acid chloride delivered ophiorrhine G. Cyclodehydratation of a protected form of the latter was followed by the desired spontaneous intramolecular Diels-Alder cycloaddition of protected ophiorrhiside E leading to ophiorrhine A, which could be converted to an unnatural product with a carbazole skeleton. We have investigated the total synthesis of pestalustaine A, a sesquiterpenoid which was isolated from an endophytic fungus pestalotiopsis adusta. We performed a ring expansion of a 6-membered intermediated to form the 7-membered core, a ring closing metathesis of a diene to construct the bridged 7/7 skeleton, and an intramolecular 1,4 addition to yield the pivotal tricyclic 7/5/6 framework. Through X-ray diffraction analysis of a crystal of an intermediate with the 7/5/6 core, we discovered that our structure differs from the one proposed in the isolation publication. By analyzing the spectra of the isolated natural product, we thought that the authors might have misassigned the structure
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