Studies on new pathways to 1,3-Diyl and their application to triquinane synthesis1,3-다이일의 새로운 합성 방법들과 트리퀴난 합성에의 응용에 관한 연구

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dc.contributor.advisorLee, Hee-Yoon-
dc.contributor.advisor이희윤-
dc.contributor.authorYoon, Yeo-Kwon-
dc.contributor.author윤여권-
dc.date.accessioned2011-12-13T04:31:27Z-
dc.date.available2011-12-13T04:31:27Z-
dc.date.issued2009-
dc.identifier.urihttp://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=309371&flag=dissertation-
dc.identifier.urihttp://hdl.handle.net/10203/31720-
dc.description학위논문(박사) - 한국과학기술원 : 화학과, 2009.2, [ v, 292 p. ]-
dc.description.abstractDevelopment 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.languageeng-
dc.publisher한국과학기술원-
dc.subject1,3-diyl-
dc.subjectlinear triquinane-
dc.subjectangular triquinane-
dc.subjecttetraquinane-
dc.subjectpentalenene-
dc.subject1,3-다이일-
dc.subject선형 트리퀴난-
dc.subject각형 트리퀴난-
dc.subject테트라퀴난-
dc.subject펜탈레넨-
dc.subject1,3-diyl-
dc.subjectlinear triquinane-
dc.subjectangular triquinane-
dc.subjecttetraquinane-
dc.subjectpentalenene-
dc.subject1,3-다이일-
dc.subject선형 트리퀴난-
dc.subject각형 트리퀴난-
dc.subject테트라퀴난-
dc.subject펜탈레넨-
dc.titleStudies on new pathways to 1,3-Diyl and their application to triquinane synthesis-
dc.title.alternative1,3-다이일의 새로운 합성 방법들과 트리퀴난 합성에의 응용에 관한 연구-
dc.typeThesis(Ph.D)-
dc.identifier.CNRN309371/325007 -
dc.description.department한국과학기술원 : 화학과, -
dc.identifier.uid020045858-
dc.contributor.localauthorLee, Hee-Yoon-
dc.contributor.localauthor이희윤-
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