DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | Lee, Hee-Seung | - |
dc.contributor.advisor | 이희승 | - |
dc.contributor.advisor | Kang, Sung-Ho | - |
dc.contributor.advisor | 강성호 | - |
dc.contributor.author | Kang, Sung-Kyoung | - |
dc.contributor.author | 강성경 | - |
dc.date.accessioned | 2015-04-23T02:22:31Z | - |
dc.date.available | 2015-04-23T02:22:31Z | - |
dc.date.issued | 2014 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=591885&flag=dissertation | - |
dc.identifier.uri | http://hdl.handle.net/10203/196468 | - |
dc.description | 학위논문(박사) - 한국과학기술원 : 화학과, 2014.8, [ vi, 88 p ] | - |
dc.description.abstract | Highly enantioselective synthesis of the key intermediate 258 to laidlomycin 1 was established. 258 was disconnected to give the left segment containing of protected anti-, syn-1,3,5-triol and the right segment containing 3 oxacycles: successive cis-, trans-THF ring and 6-memebered cyclic ketal.The backbone of right segment (C11-26) was achieved by two B-alkyl Suzuki-Miyaura coupling reactions. The requisite stereochemistry at C12 and C13 were secured by desymmetric benzoylation and Roush allylation respectively. cis-THF ring was obtained via both osmate-mediated oxidative cyclization route and VO(acac)2-mediated epoxidation followed by acidic cyclization route with (Z)-alkene. Shi epoxidation with (E)-alkene followed by acidic cyclization and oxidative lactonization in Anelli’s conditioin furnished desired trans-THF and lactone with high diastereoselectivity. The right segment 85 was synthesized from desymmetric benzoylation of 2-methylpropane-1,2,3-triol over 26 steps in 15% overall yield via two different epoxidation route.The left segment (C1-C10) was synthesized via Evans aldol reaction and anti-aldol coupling. The reduction of β-hydroxy ketone to anti-alcohol was conducted successfully via Evans-Tishchenko method to give 222 as a major with a 26 : 1 d.r..The key intermediate 258 was obtained in high yield via Horner-Wadsworth-Emmons reaction of 85 and β-ketophosphonate 257 derived from 222. | eng |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | B-alkyl Suzuki-Miyaura coupling | - |
dc.subject | Shi epoxidation | - |
dc.subject | oxidative lactonization | - |
dc.subject | Evans aldol reaction | - |
dc.subject | Evans-Tishchenko reduction | - |
dc.subject | 레이드로마이신 | - |
dc.subject | B-알킬 스즈키 커플링 | - |
dc.subject | 비대칭화 벤조일레이션 | - |
dc.subject | shi 에폭시화 반응 | - |
dc.subject | Evans-Tishchenko 환원 | - |
dc.subject | Evans 알돌 | - |
dc.subject | 산화성 락톤화 반응 | - |
dc.subject | Laidlomycin | - |
dc.subject | Horner-Wadsworth-Emmons reaction | - |
dc.title | Synthetic studies on laidlomycin | - |
dc.title.alternative | 레이드로마이신의 합성에 관한 연구 | - |
dc.type | Thesis(Ph.D) | - |
dc.identifier.CNRN | 591885/325007 | - |
dc.description.department | 한국과학기술원 : 화학과, | - |
dc.identifier.uid | 020087002 | - |
dc.contributor.localauthor | Lee, Hee-Seung | - |
dc.contributor.localauthor | 이희승 | - |
dc.contributor.localauthor | Kang, Sung-Ho | - |
dc.contributor.localauthor | 강성호 | - |
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