DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Lee, Hee-Yoon | - |
dc.contributor.advisor | 이희윤 | - |
dc.contributor.author | Ham, Jin-Su | - |
dc.contributor.author | 함진수 | - |
dc.date.accessioned | 2011-12-13T04:51:47Z | - |
dc.date.available | 2011-12-13T04:51:47Z | - |
dc.date.issued | 2009 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=327358&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/32120 | - |
dc.description | 학위논문(석사) - 한국과학기술원 : 화학과, 2009. 8., [ iii, 113 p. ] | - |
dc.description.abstract | Cycloaddition reaction, which can make two new bonds in regio- and stereocontrolled fashion, are very useful methods in organic synthesis. Among the various types of cycloadditions, dipolar cycloadditions of oxidopyrylium species and the related carbonyl ylides have proved to be a powerful methodology for the synthesis. The intramolecular [5+2] cycloaddition reaction of oxidopyrylium ion generated from acetoxypyranone produced fuzed 6 and 7-membered ring regio- and stereoselectively. This method provides a good synthetic strategy to construct norsesquiterpenoid core structure like biological active frondosins. Asymmetric total synthesis of frondosin A, which is fuzed 6 and 7-membered ring and cis-phenyl and contain methyl functional group, was successfully utilized regio- and stereoselectively by using oxidopyrylium ion [5+2] cycloaddition. In our synthetic trials, we could know that gem-dimethyl group affected reaction rate and diastereomer ratio, and aromatic group affected the face selectivity of cycloaddition. Specially, methoxy group of ortho-position in aromatic substituent was very important in view of face selectivity during [5+2] cycloaddition reaction of oxidopyrylium. Azabicyclo[3.3.0]octane derivative, which exhibit nicotinic pharmacology with a beneficial effect, but without significant associated side effect was successfully synthesized through 5 step from isobutyric acid. Design of processes is to maximize the amount of raw material that ends up in the product and the design of energy efficient processes. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | frondosin | - |
dc.subject | oxidopyrylium | - |
dc.subject | 프론도신 | - |
dc.subject | 옥시도피릴륨 | - |
dc.subject | frondosin | - |
dc.subject | oxidopyrylium | - |
dc.subject | 프론도신 | - |
dc.subject | 옥시도피릴륨 | - |
dc.title | Studies toward the asymmetric total synthesis of frondosin A through oxydopyrylium [5+2] cycloaddition reaction | - |
dc.title.alternative | 옥시도피릴륨 이온의 [5+2] 고리화 첨가반응을 통한 프론도신 A의 비대칭 전합성에 대한 연구 | - |
dc.type | Thesis(Master) | - |
dc.identifier.CNRN | 327358/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 020074222 | - |
dc.contributor.localauthor | Lee, Hee-Yoon | - |
dc.contributor.localauthor | 이희윤 | - |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.