DC Field | Value | Language |
---|---|---|
dc.contributor.author | Liu, P | ko |
dc.contributor.author | Hong, Sungwoo | ko |
dc.contributor.author | Weinreb, SM | ko |
dc.date.accessioned | 2013-03-07T17:11:33Z | - |
dc.date.available | 2013-03-07T17:11:33Z | - |
dc.date.created | 2012-02-06 | - |
dc.date.created | 2012-02-06 | - |
dc.date.issued | 2008-06 | - |
dc.identifier.citation | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.130, no.24, pp.7562 - 7562 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10203/90752 | - |
dc.description.abstract | The first enantioselective total synthesis of the rearranged Securinega alkaloid (-)-secu'amamine A is reported starting from D-proline as the source of absolute chirality. The syntheis requires 15 steps starting from D-proline-derived N-trityl aldehyde 11 and proceeds in approximately 9% overall yield. Key steps include a stereoselective conjugate addition of pyrrolidino enedione 19 to afford indolizidine 24 as the major product and cyclization/lactonization of diketoester 25 to produce tetracycle 26. In addition, (1)H NMR NOE studies and X-ray analysis on the synthetic alkaloid have established that the indolizidine moiety is trans-fused. | - |
dc.language | English | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.subject | SUFFRUTICOSA VAR. AMAMIENSIS | - |
dc.subject | CONFORMATIONAL-ANALYSIS | - |
dc.subject | CHIRAL ALKENES | - |
dc.subject | SECUAMAMINE-A | - |
dc.subject | MODEL | - |
dc.title | Total synthesis of the Securinega alkaloid (-)-secuamamine A | - |
dc.type | Article | - |
dc.identifier.wosid | 000256671400023 | - |
dc.identifier.scopusid | 2-s2.0-45249097976 | - |
dc.type.rims | ART | - |
dc.citation.volume | 130 | - |
dc.citation.issue | 24 | - |
dc.citation.beginningpage | 7562 | - |
dc.citation.endingpage | 7562 | - |
dc.citation.publicationname | JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | - |
dc.identifier.doi | 10.1021/ja802700z | - |
dc.contributor.localauthor | Hong, Sungwoo | - |
dc.contributor.nonIdAuthor | Liu, P | - |
dc.contributor.nonIdAuthor | Weinreb, SM | - |
dc.type.journalArticle | Article | - |
dc.subject.keywordPlus | SUFFRUTICOSA VAR. AMAMIENSIS | - |
dc.subject.keywordPlus | CONFORMATIONAL-ANALYSIS | - |
dc.subject.keywordPlus | CHIRAL ALKENES | - |
dc.subject.keywordPlus | SECUAMAMINE-A | - |
dc.subject.keywordPlus | MODEL | - |
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