Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized C‑Glycosides
A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated...
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| Veröffentlicht in: | Journal of organic chemistry 2013-06, Vol.78 (11), p.5160-5171 |
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| container_end_page | 5171 |
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| container_issue | 11 |
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| container_title | Journal of organic chemistry |
| container_volume | 78 |
| creator | Gerard, Baudouin Lee, Maurice D Dandapani, Sivaraman Duvall, Jeremy R Fitzgerald, Mark E Kesavan, Sarathy Lowe, Jason T Marié, Jean-Charles Pandya, Bhaumik A Suh, Byung-Chul O’Shea, Morgan Welzel Dombrowski, Michael Hamann, Diane Lemercier, Berenice Murillo, Tiffanie Akella, Lakshmi B Foley, Michael A Marcaurelle, Lisa A |
| description | A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis. |
| doi_str_mv | 10.1021/jo4000916 |
| format | Article |
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Org. Chem</addtitle><description>A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis.</description><subject>Glycosides - chemical synthesis</subject><subject>Glycosides - chemistry</subject><subject>moieties</subject><subject>Molecular Conformation</subject><subject>organic chemistry</subject><subject>Pyrans - chemistry</subject><subject>stereochemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9u1DAQxq0K1G4LB14A5YJEDwH_iZ34goSWtiBVQmLhbLnOpOvFiVtPUimc-gp9xT4Jhi0rKiFxGs3Mbz7NzEfIC0bfMMrZ202sKKWaqT2yYJLTUmlaPSELSjkvBVfigBwibjJDpZT75IALpTmr2IJsVvMwrgE9FrErViMkiG4NvXc2hLmwQ1usvkOA8Xf6wd9AQihOJ4S2-OKHy2I14wg9Fl2Kfa4PbvRxsMH_yMDy_vbuLMwuom8Bn5GnnQ0Izx_iEfl2evJ1-bE8_3z2afn-vLSVaMaSXVTWtpWkjaDadaqTtVBWSOp4pQQ0NVd1LYUTWjfK6Y4q4A3LzVZqyToljsi7re7VdNFD62AYkw3mKvneptlE683jzuDX5jLeGFFLrpomC7x-EEjxegIcTe_RQQh2gDih4ds_Nlz9F2VCSa2pYFVGj7eoSxExQbfbiFHzy0azszGzL_8-YUf-8S0Dr7aAdZjnppRfjv8Q-gmNw6UI</recordid><startdate>20130607</startdate><enddate>20130607</enddate><creator>Gerard, Baudouin</creator><creator>Lee, Maurice D</creator><creator>Dandapani, Sivaraman</creator><creator>Duvall, Jeremy R</creator><creator>Fitzgerald, Mark E</creator><creator>Kesavan, Sarathy</creator><creator>Lowe, Jason T</creator><creator>Marié, Jean-Charles</creator><creator>Pandya, Bhaumik A</creator><creator>Suh, Byung-Chul</creator><creator>O’Shea, Morgan Welzel</creator><creator>Dombrowski, Michael</creator><creator>Hamann, Diane</creator><creator>Lemercier, Berenice</creator><creator>Murillo, Tiffanie</creator><creator>Akella, Lakshmi B</creator><creator>Foley, Michael A</creator><creator>Marcaurelle, Lisa A</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20130607</creationdate><title>Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized C‑Glycosides</title><author>Gerard, Baudouin ; 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| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2013-06, Vol.78 (11), p.5160-5171 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Glycosides - chemical synthesis Glycosides - chemistry moieties Molecular Conformation organic chemistry Pyrans - chemistry stereochemistry Stereoisomerism |
| title | Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized C‑Glycosides |
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