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Enantio- and Stereospecific Syntheses of 15(R)-Me-PGD2, A Potent and Selective DP2−Receptor Agonist

Autor: Joshua Rokach, Gail E. Grant, Pranav Patel, William S. Powell, Gue-Jae Lee, Seongjin Kim

Publikováno v: The Journal of Organic Chemistry. 73:7213-7218

The first total synthesis of 15(R)-Me-PGD2 3 is reported. The synthesis is based on the enantioselective and stereospecific syntheses of synthon 17 and its attachment to the five-membered ring by a olefin cross metathesis reaction. This approach perm

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0b30163e9109e18d6d306b50b8d6ee3b
https://doi.org/10.1021/jo801190m

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Airway epithelial cells synthesize the lipid mediator 5-oxo-ETE in response to oxidative stress

Autor: Joshua Rokach, Gue-Jae Lee, Chantal Cossette, Alain Lesimple, Sylvie Gravel, Goutam Saha, William S. Powell, Karl-Rudolf Erlemann

Publikováno v: Free Radical Biology and Medicine. 42:654-664

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a potent eosinophil chemoattractant that is synthesized from the 5-lipoxygenase product 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by the NADP+-dependent enzyme 5-hydroxyeicosanoid dehydro

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::93830ee3ac112b5817f56d6914622fb0
https://doi.org/10.1016/j.freeradbiomed.2006.12.006

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Agonist and Antagonist Effects of 15R-Prostaglandin (PG) D2and 11-Methylene-PGD2on Human Eosinophils and Basophils

Autor: William S. Powell, Chantal Cossette, Seongjin Kim, Joshua Rokach, Gue-Jae Lee, Sinead E Walsh, Sophie Bellone, John A. Lawson

Publikováno v: Journal of Pharmacology and Experimental Therapeutics. 320:173-179

Prostaglandin (PG) D2 acts through both the DP(1) receptor, which is coupled to adenylyl cyclase, and the DP2 receptor (chemoattractant receptor-homologous molecule expressed on Th2 cells), which is present on eosinophils, basophils, and Th2 cells an

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::41de1baced8ad1076f260119a47e9ca1
https://doi.org/10.1124/jpet.106.111062

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Total Synthesis of 8,12-iso-iPF3α-VI, an EPA-Derived Isoprostane: Stereoselective Introduction of the Fifth Asymmetric Center

Autor: Chih-Tsung Chang, John A. Lawson, Domenico Pratico, Joshua Rokach, Sheila H. Jacobo, Gue-Jae Lee, Garret A. FitzGerald, William S. Powell

Publikováno v: The Journal of Organic Chemistry. 71:1370-1379

[reaction: see text] A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereoch

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::809ce5259d2c23ab049195485073245a
https://doi.org/10.1021/jo051916x

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l-Valinol and l-phenylalaninol-derived 2-phenylamino-2-oxazolines as chiral auxiliaries in asymmetric alkylations

Autor: Uk Lee, Jae Nyoung Kim, Taek Hyeon Kim, Gue-Jae Lee

Publikováno v: Tetrahedron: Asymmetry. 13:9-12

Lithium enolates of N-acyl phenyliminooxazolidine auxiliaries reacted with alkyl halides to produce the α-alkylated products with very high diastereofacial selectivity (up to >99% d.e.). The products were readily cleaved by simple alkaline hydrolysi

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::c0ff8233617d88225a25e23756446328
https://doi.org/10.1016/s0957-4166(02)00044-7

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A mild cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas to 2-phenylamino-2-oxazolines using TsCl/NaOH

Autor: Namgun Lee, Gue-Jae Lee, Taek Hyeon Kim, Jae Nyoung Kim

Publikováno v: Tetrahedron. 57:7137-7141

An efficient synthesis of 2-phenylamino-2-oxazolines 3 via cyclodesulfurization of N-(2-hydroxyethyl)-N′-phenylthioureas 2 by a one-pot reaction using p-toluenesulfonyl chloride (TsCl) and NaOH in very good yields is described.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::22b96ab6ccf48b8c4d16ce08eb62dcab
https://doi.org/10.1016/s0040-4020(01)00682-2

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l-Valinol and l-phenylalaninol-derived 2-imidazolidinones as chiral auxiliaries in asymmetric aldol reactions

Autor: Gue-Jae Lee, Taek Hyeon Kim

Publikováno v: Tetrahedron Letters. 41:1505-1508

The chiral N -propionyl-2-imidazolidinones were synthesized in three steps from l -valinol and l -phenylalaninol and the aldol reaction of their boron enolate with aldehydes proceeded with high diastereoselectivity.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::547e45793684387a1dbb12c5ebcb0c1f
https://doi.org/10.1016/s0040-4039(99)02325-4

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One-pot synthesis of 2-phenylaminothiazolines from N-2-hydroxyethyl)-N′-phenylthioureas

Autor: Jung Ki Min, Gue-Jae Lee, Taek Hyeon Kim

Publikováno v: Tetrahedron Letters. 40:8201-8204

2-Phenylaminothiazolines 3 were synthesized from N -(2-hydroxyethyl)- N′ -phenylthioureas 2 by a one-pot reaction using p -toluenesulfonyl chloride (TsCl) and NaOH or Et 3 N.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::d0e6588bebf2a0cbab8978a834e01dfe
https://doi.org/10.1016/s0040-4039(99)01704-9

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Investigation of the Mitsunobu Reaction ofN-(2-Hydroxyethyl)-N′-Phenyl-Ureas

Autor: Taek Hyeon Kim, Gue-Jae Lee, Mi-Hyun Cha

Publikováno v: Synthetic Communications. 29:2753-2758

The Mitsunobu reaction of N-(2-hydroxyethyl)-ureas 1 using PPh3 and EtO2CN[dbnd]NCO2Et led to the mixture of N- and O-alkylation products or a single isomer depending on the substrates.

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::f12cc907575006f519e3f10ff9854018
https://doi.org/10.1080/00397919908086441

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