A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine
Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantio...
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| Veröffentlicht in: | Journal of organic chemistry 2010-01, Vol.75 (1), p.178-189 |
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| container_end_page | 189 |
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| container_issue | 1 |
| container_start_page | 178 |
| container_title | Journal of organic chemistry |
| container_volume | 75 |
| creator | Amat, Mercedes Llor, Núria Checa, Begoña Molins, Elies Bosch, Joan |
| description | Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group. |
| doi_str_mv | 10.1021/jo902346j |
| format | Article |
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Enantioselective Total Synthesis of (−)-16-Episilicine</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. 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Enantioselective Total Synthesis of (−)-16-Episilicine</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-01-01</date><risdate>2010</risdate><volume>75</volume><issue>1</issue><spage>178</spage><epage>189</epage><pages>178-189</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Starting from an appropriate unsaturated phenylglycinol-derived oxazolopiperidone lactam, the synthesis of (−)-16-episilicine is reported, the key steps being a stereoselective conjugate addition, a stereoselective alkylation, and a ring-closing metathesis reaction. This represents the first enantioselective total synthesis of an alkaloid of the silicine group.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>19968261</pmid><doi>10.1021/jo902346j</doi><tpages>12</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Journal of organic chemistry, 2010-01, Vol.75 (1), p.178-189 |
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| language | eng |
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| subjects | Alkaloids - chemical synthesis Alkaloids - chemistry Catalysis Chemistry Contraindications Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Lactams - chemistry Molecular Structure Organic chemistry Preparations and properties Secologanin Tryptamine Alkaloids |
| title | A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (−)-16-Episilicine |
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