DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Kang, Sung-Ho | - |
dc.contributor.advisor | 강성호 | - |
dc.contributor.author | Lee, Hee-Seung | - |
dc.contributor.author | 이희승 | - |
dc.date.accessioned | 2011-12-13T04:52:35Z | - |
dc.date.available | 2011-12-13T04:52:35Z | - |
dc.date.issued | 1992 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=59916&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/32173 | - |
dc.description | 학위논문(석사) - 한국과학기술원 : 화학과, 1992.2, [ ii, 51 p. ] | - |
dc.description.abstract | A highly stereoselective synthesis of the key intermediate $\underline{99}$ of 1-$\beta$-methylcabapenem antibiotics was accomplished in overall 14 steps in 8 reaction pots starting from commercially available (R)-(-)-3-bromo-2-methyl-1-propanol $\underline{67}$. Starting alcohol $\underline{71c}$ was readily obtained from trimethylsilyl ether of $\underline{67}$ in one pot reaction in 51\% overall yield. Alcohol $\underline{71c}$ was subjected to Swern oxidation followed by nitrone formation with N-benzylhydroxylamine and 1,3-dipolar cycloaddition effected the formation of isoxazolidine $\underline{93a}$ in 71\% overall yield with high diastereoselectivity(24:1). Deacetylation, oxidation, enol ether formation and catalytic osmylation in sequence provided $\alpha$-hydroxy ketone $\underline{98}$ in 70\% overall yield. $\underline{98}$ was subjected to oxidative cleavage and reduction followed by cyclization in one pot to furnish the desired key intermediate to 1-$\beta$-methylcabapenem 2, N-benzylated azetidinone $\underline{99}$ in 57\% overall yield. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.title | Synthetic studies on 1-β-methylcabapenem | - |
dc.title.alternative | 1-β-메틸카바페넴의 합성에 관한 연구 | - |
dc.type | Thesis(Master) | - |
dc.identifier.CNRN | 59916/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 000901432 | - |
dc.contributor.localauthor | Kang, Sung-Ho | - |
dc.contributor.localauthor | 강성호 | - |
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