Access to Isocarbacyclin Derivatives via Substrate-Controlled Enolate Formation:  Total Synthesis of 15-Deoxy-16-(<i>m</i>-tolyl)- 17,18,19,20-tetranorisocarbacyclin

Sheddan, Neil A.; Mulzer, Johann

doi:10.1021/ol0515762

Cited by 18 publications

(14 citation statements)

References 18 publications

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“…All starting materials were commercially available and used without any purification. Compounds 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h , 3i , 3j , 3k , 3l , 5a , 6a , 7a , 8a , 9a , 5b , 6b , 6d , and 13a were reported previously. High-resolution mass spectra were performed at the Global Facility Center, Hokkaido University.…”

Section: Methodssupporting

confidence: 57%

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

et al. 2020

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The development of a C2-extension of primary alcohols with ethanol as the C2 source and catalysis by [Cp*IrCl 2 ] 2 (where Cp* = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.

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Section: Methodssupporting

confidence: 57%

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

et al. 2020

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“…18,19, was synthesized using a novel -side chain addition strategy as detailed previously (Sheddan and Mulzer, 2005;Sheddan et al, 2007). 3-Benzyl-5-(6-carboxyhexyl)-1-(2-cyclohexyl-2-ydroxyethylamino) hydantoin (BWA A868C), PGE 2 , and iloprost were purchased from Cayman Chemicals (Ann Arbor, MI).…”

Section: Methodsmentioning

confidence: 99%

Evidence for a Second Receptor for Prostacyclin on Human Airway Epithelial Cells That Mediates Inhibition of CXCL9 and CXCL10 Release

Wilson

Sheddan²,

Newton³

et al. 2010

Mol Pharmacol

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Herein we provide evidence for the coexpression of two distinct prostacyclin (PGI 2 ) receptors (IP) on BEAS-2B human airway epithelial cells. IP receptor heterogeneity initially was suggested by the finding that the rank orders of potency of PGI 2 and three structurally similar analogs [taprostene, iloprost,18,19,] for the inhibition of chemokine (CXCL9 and CXCL10) release and for transcriptional activation/augmentation of cAMP response element and glucocorticoid response element luciferase reporters were distinct. Indeed, PGI 2 , taprostene, and iloprost activated both reporters whereas 15-deoxy-TIC was inert. Conversely, 15-deoxy-TIC, PGI 2 , and taprostene (but not iloprost) suppressed chemokine release. Further experiments established that iloprost did not antagonize the inhibitory effect taprostene or 15-deoxy-TIC on chemokine output. Likewise, 15-deoxy-TIC failed to antagonize taprostene-and iloprost-induced reporter transactivation. Thus, iloprost-and 15-deoxy-TIC-induced responses were apparently mediated via pharmacologically distinct receptors. In human embryonic kidney 293 cells overexpressing the human recombinant IP receptor receptor, 15-deoxy-TIC was considerably less potent (Ͼ10,000-fold) than iloprost and taprostene in promoting cAMP accumulation, yet in BEAS-2B cells, these analogs were equipotent. IP receptor heterogeneity was also supported by the finding that the affinity of the IP receptor antagonist R-3-(4-fluorophenyl)-2-[5-(4-fluorophenyl)-benzofuran-2-yl-methoxycarbonyl-amino] propionic acid (RO3244794) for the receptor mediating inhibition of chemokine release was approximately 10-fold lower than for the receptor mediating both transcriptional outputs. Finally, small interfering RNAs directed against the IP receptor gene, PTGIR, failed to block the suppression of chemokine output induced by taprostene and 15-deoxy-TIC, whereas taprostene-and iloprostinduced transcriptional responses were markedly attenuated. Collectively, these results indicate that PGI 2 , taprostene and 15-deoxy-TIC suppress chemokine release from BEAS-2B cells by interacting with a novel IP receptor that we denote here as the "IP 2 " subtype.

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“…Palladiumcatalyzed coupling of lithium tri(2-oxazolyl)magnesate and tri(2-benzoxazolyl)magnesates with arylhalides [102]. A palladium-catalyzed alkyl Grignard-alkenyl triflate coupling was used in a synthesis of 15-deoxy-16-(m-tolyl)-17,18,19,20-tetranorisocarbacyclin [103].…”

Section: Carbon-carbon Bond-forming Reactions Via Transmetallationmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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Access to Isocarbacyclin Derivatives via Substrate-Controlled Enolate Formation: Total Synthesis of 15-Deoxy-16-(m-tolyl)- 17,18,19,20-tetranorisocarbacyclin

Cited by 18 publications

References 18 publications

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

Evidence for a Second Receptor for Prostacyclin on Human Airway Epithelial Cells That Mediates Inhibition of CXCL9 and CXCL10 Release

Transition metals in organic synthesis: Highlights for the year 2005

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