DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Lee, Hee-Yoon | - |
dc.contributor.advisor | 이희윤 | - |
dc.contributor.author | Yoon, Yeo-Kwon | - |
dc.contributor.author | 윤여권 | - |
dc.date.accessioned | 2011-12-13T04:31:27Z | - |
dc.date.available | 2011-12-13T04:31:27Z | - |
dc.date.issued | 2009 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=309371&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/31720 | - |
dc.description | 학위논문(박사) - 한국과학기술원 : 화학과, 2009.2, [ v, 292 p. ] | - |
dc.description.abstract | Development of new pathways to 1,3-diyl for cycloaddition reaction to construct various polyquinane frameworks has been studied. The intramolecular [2+3] cycloaddition reaction of the 1,3-trimethylenemethane(TMM) diyl generated from the intramolecular cyclopropanation reaction of alkylidene carbene produced linearly, angularly fused triquinanes and tetaquinanes regio- and stereoselectively. This method provides a good synthetic strategy to construct polyquinane skeletons. However, it exhibits the several disadvantages such as 1,2-shift of alkylidene carbene and relatively low product yield. Therefore, alternative generation method of 1,3-diyl was needed to apply for the construction of polyquinane skeleton. A new efficient way to generate 1,3-trimethylenemethane(TMM) diyl was developed with allene and N-aziridinylimine or with allene and N-tosylhydrazone sodium salt. This synthetic strategy was successfully utilized in [2+3] cycloaddition reaction with olefin in high yield. The novel one pot sequential transformation of thermally labile pyrazole obtained through [2+3] cycloaddition reaction of diazoalkane with allene produced 1,3-trimethylenemethane(TMM) diyl and the generated diyl was trapped by olefin to form polyquinane framework. Total Synthesis of dl-pentalenene, angular triquinane natural product, was successful through 11 steps from (E)-2-methylhept-5-en-1-ol. Triquinane core structure was assembled by thermolysis of allenyl N-tosylhydrazone sodium salt. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | 1,3-diyl | - |
dc.subject | linear triquinane | - |
dc.subject | angular triquinane | - |
dc.subject | tetraquinane | - |
dc.subject | pentalenene | - |
dc.subject | 1,3-다이일 | - |
dc.subject | 선형 트리퀴난 | - |
dc.subject | 각형 트리퀴난 | - |
dc.subject | 테트라퀴난 | - |
dc.subject | 펜탈레넨 | - |
dc.subject | 1,3-diyl | - |
dc.subject | linear triquinane | - |
dc.subject | angular triquinane | - |
dc.subject | tetraquinane | - |
dc.subject | pentalenene | - |
dc.subject | 1,3-다이일 | - |
dc.subject | 선형 트리퀴난 | - |
dc.subject | 각형 트리퀴난 | - |
dc.subject | 테트라퀴난 | - |
dc.subject | 펜탈레넨 | - |
dc.title | Studies on new pathways to 1,3-Diyl and their application to triquinane synthesis | - |
dc.title.alternative | 1,3-다이일의 새로운 합성 방법들과 트리퀴난 합성에의 응용에 관한 연구 | - |
dc.type | Thesis(Ph.D) | - |
dc.identifier.CNRN | 309371/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 020045858 | - |
dc.contributor.localauthor | Lee, Hee-Yoon | - |
dc.contributor.localauthor | 이희윤 | - |
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