Academic literature on the topic 'Integramycin'

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Journal articles on the topic "Integramycin"

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Prusov, Evgeny V. "Synthesis of the spiroketal core of integramycin." Beilstein Journal of Organic Chemistry 9 (November 12, 2013): 2446–50. http://dx.doi.org/10.3762/bjoc.9.282.

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A concise synthetic strategy towards the spiroketal core of the HIV-integrase inhibitor integramycin (1) was developed. The required ketone precursor was efficiently constructed from two simple and easily accessible subunits by means of a hydrozirconation/copper catalyzed acylation reaction. The effects of different protecting groups on the spiroketalization step were also investigated.
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2

Sun, Huikai, Jason R. Abbott, and William R. Roush. "Stereoselective Synthesis of a Model C(18)–C(35) Spiroketal Fragment of Integramycin." Organic Letters 13, no. 10 (May 20, 2011): 2734–37. http://dx.doi.org/10.1021/ol200834p.

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3

Dineen, Thomas A., and William R. Roush. "Stereoselective Synthesis of the Octahydronaphthalene Unit of Integramycin via an Intramolecular Diels−Alder Reaction." Organic Letters 7, no. 7 (March 2005): 1355–58. http://dx.doi.org/10.1021/ol050191g.

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4

Wang, Lijun, and Paul E. Floreancig. "Synthesis of the C16−C35 Fragment of Integramycin Using Olefin Hydroesterification as a Linchpin Reaction." Organic Letters 6, no. 4 (February 2004): 569–72. http://dx.doi.org/10.1021/ol036339i.

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5

Singh, Sheo B., Deborah L. Zink, Brian Heimbach, Olga Genilloud, Ana Teran, Keith C. Silverman, Russell B. Lingham, Peter Felock, and Daria J. Hazuda. "Structure, Stereochemistry, and Biological Activity of Integramycin, a Novel Hexacyclic Natural Product Produced byActinoplanessp. that Inhibits HIV-1 Integrase." Organic Letters 4, no. 7 (April 2002): 1123–26. http://dx.doi.org/10.1021/ol025539b.

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Singh, Sheo B., Deborah L. Zink, Brian Heimbach, Olga Genilloud, Ana Teran, Keith C. Silverman, Russell B. Lingham, Peter Felock, and Daria J. Hazuda. "ChemInform Abstract: Structure, Stereochemistry, and Biological Activity of Integramycin, a Novel Hexacyclic Natural Product Produced by Actinoplanes sp. that Inhibits HIV-1 Integrase." ChemInform 33, no. 35 (May 20, 2010): no. http://dx.doi.org/10.1002/chin.200235239.

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7

Dineen, Thomas A., and William R. Roush. "Stereoselective Synthesis of the Octahydronaphthalene Unit of Integramycin (I) via an Intramolecular Diels—Alder Reaction." ChemInform 36, no. 33 (August 16, 2005). http://dx.doi.org/10.1002/chin.200533265.

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Dissertations / Theses on the topic "Integramycin"

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Rosin, Thomas [Verfasser]. "Studien zur Totalsynthese von Integramycin / Thomas Rosin." Hannover : Gottfried Wilhelm Leibniz Universität Hannover, 2020. http://d-nb.info/1220422118/34.

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2

Fischer, Joshua. "HIV-1 Integrase Inhibitors: A Formal Total Synthesis of Lithospermic Acid And Synthetic Studies Towards Integramycin." University of Sydney, 2007. http://hdl.handle.net/2123/2397.

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Doctor of Philosophy (PhD)
This thesis describes synthetic studies towards the HIV-1 integrase inhibitory natural products lithospermic acid and integramycin, resulting in a formal total synthesis of the former. A modular, flexible and convergent synthetic strategy to lithospermic acid was devised. In this approach, a Sonogashira coupling was used to unite the C1–C7 and C20–C27 fragments that were subsequently manipulated to then participate in the key step of the synthesis, a palladium-mediated carbonylative annulation. Reduction of the benzofuran nucleus with magnesium in methanol then provided the desired dihydrobenzofuran core of lithospermic acid. Various protecting group strategies were investigated to complete this sequence in an efficient manner. Further synthetic manipulations afforded the complete C1–C9/C19–C27 fragment, which was united with the C10–C18 fragment to deliver the entire carbon skeleton of lithospermic acid. A two step deprotection sequence was undertaken, however, complications with the final deprotective step prevented definitive proof that the total synthesis of lithospermic acid had been achieved. An alternate protecting group strategy was sought, and a formal total synthesis of lithospermic acid was achieved by intercepting an advanced intermediate from a previous total synthesis. Several strategies for the enantioselective synthesis of the dihydrobenzofuran core of lithospermic acid were evaluated, however, none proved successful. A synthetic route towards the tetramic acid subunit of integramycin was also investigated. 3- Methoxymaleimide was constructed using known chemistry, and the regioselective reduction of this ring system was developed. Attempts to further functionalise this ring system were thwarted by difficulties associated with handling. The scope of the regioselective reduction was investigated on an array of N- substituted methoxymaleimides with the procedure found to be generally high yielding and highly regioselective.
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