DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Kang, Sung-Ho | - |
dc.contributor.advisor | 강성호 | - |
dc.contributor.author | Jun, Hyuk-Sang | - |
dc.contributor.author | 전혁상 | - |
dc.date.accessioned | 2011-12-13T05:01:28Z | - |
dc.date.available | 2011-12-13T05:01:28Z | - |
dc.date.issued | 1997 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=112879&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/32772 | - |
dc.description | 학위논문(석사) - 한국과학기술원 : 화학과, 1997.2, [ ii, 32 p. ] | - |
dc.description.abstract | For the synthesis of (+)-lactacystin 1, the key intermediate,(3R,4S)-5,5- dihydroxymethyl-4-hydroxy-3-methylpyrrolidone 48, has been synthesized effectively via aminomercuration of allylic trichloroacetimidate 65. Epoxide 64 was prepared by the known procedure from methyl (s)-(+)-3- hydroxy-2-methylpropionate over 6 steps in 48% overall yield. Allylic diol 60 was readily obtained by the opening of the epoxide ring in 64 in 75% yield. Mercurals 85 was elaborated via aminomercuration of allylic trichloro- acetimidate 65 derived from allylic diol 60 in 85% yield. Treatment of 85 with TEMPO in the presence of lithium borohydride introduced the hydroxy group successfully to furnish oxazolines 87 in 85% yield. Amides 94 were obtained from 87 by deprotection,acetylation and diol protection in sequence in 67\% yield. Amides 94 were debenzylated and the resulting primary alcohols were oxidized to provide carboxylic acids 97. γ-Lactam 98 and 99 were prepared by deprotection of amide group of 97 and the cyclization of γ-aminoacids. The reductive cleavage of N-O bonds and the concomitant hydrolysis of acetonide groups in 98 and 99 provided the triol γ-lactam 48 in 82% yield. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | (3R,4S)-5,5-dihydroxymethyl-4-hydroxy-3-methylpyrrolidone | - |
dc.subject | (3R,4S)-5,5-디하이드록시메틸-4-하이드록시-3-메틸피롤리돈 | - |
dc.title | Synthesis of (3R,4S)-5,5-dihydroxymethyl-4-hydroxy-3-methylpyrrolidone | - |
dc.title.alternative | (3R,4S)-5,5-디하이드록시메틸-4-하이드록시-3-메틸피롤리돈의 합성에 관한 연구 | - |
dc.type | Thesis(Master) | - |
dc.identifier.CNRN | 112879/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 000953542 | - |
dc.contributor.localauthor | Kang, Sung-Ho | - |
dc.contributor.localauthor | 강성호 | - |
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