DC Field | Value | Language |
---|---|---|
dc.contributor.author | Yoo, DJ | - |
dc.contributor.author | Choi, W | - |
dc.contributor.author | Lee, SJ | - |
dc.contributor.author | Ahn, KH | - |
dc.date.accessioned | 2016-03-31T14:23:01Z | - |
dc.date.available | 2016-03-31T14:23:01Z | - |
dc.date.created | 2009-08-12 | - |
dc.date.issued | 1996-02-20 | - |
dc.identifier.issn | 0253-2964 | - |
dc.identifier.other | 1996-OAK-0000009354 | - |
dc.identifier.uri | https://oasis.postech.ac.kr/handle/2014.oak/21624 | - |
dc.description.abstract | The synthesis of common skeleton of podosporin A and aureol was studied through cationic olefin cyclization as a key step. The generation of thermodynamic silyl enol ether or enol acetate under known conditions gave regioselectivity of 88:12. The enolate alkylation of 2,3-dimethylcyclohexanone with 2,5-dimethoxybenzyl bromide at the more substituted site via lithium enolate gave poor yield. In this case an organozincate or an ammonium enolate also proved to be ineffective or not practical in terms of yield. Side chain elongation of the substituted cyclohexanone 13 through Grignard reaction, Wittig reaction, or Shappiro reaction did not proceed because of steric hindrance and side reactions. However, Stille coupling reaction via enol triflate produced the desired product 18 in high yield. The advanced intermediate 22, which was efficiently synthesized from 18, produced 24 instead of the desired product under a cationic olefin cyclization condition, indicating that the cyclization occurred in a stepwise manner via the organomercury intermediate 23. | - |
dc.description.statementofresponsibility | X | - |
dc.language | English | - |
dc.publisher | KOREAN CHEMICAL SOC | - |
dc.relation.isPartOf | BULLETIN OF THE KOREAN CHEMICAL SOCIETY | - |
dc.subject | ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS | - |
dc.subject | CONJUGATE ADDITION | - |
dc.subject | ORGANOCOPPER REAGENTS | - |
dc.subject | ETHERS | - |
dc.subject | CYCLIZATIONS | - |
dc.subject | ALKYLATION | - |
dc.subject | CHEMISTRY | - |
dc.subject | COMPLEX | - |
dc.subject | KETONES | - |
dc.subject | ALKENES | - |
dc.title | A synthetic study on (+/-)-podosporin A | - |
dc.type | Article | - |
dc.contributor.college | 분자소재융합계의 전자-광 거동연구센터 | - |
dc.author.google | Yoo, DJ | - |
dc.author.google | Choi, W | - |
dc.author.google | Lee, SJ | - |
dc.author.google | Ahn, KH | - |
dc.relation.volume | 17 | - |
dc.relation.issue | 2 | - |
dc.relation.startpage | 153 | - |
dc.relation.lastpage | 158 | - |
dc.contributor.id | 10087916 | - |
dc.relation.journal | BULLETIN OF THE KOREAN CHEMICAL SOCIETY | - |
dc.relation.index | SCI급, SCOPUS 등재논문 | - |
dc.relation.sci | SCI | - |
dc.collections.name | Journal Papers | - |
dc.type.rims | ART | - |
dc.identifier.bibliographicCitation | BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.17, no.2, pp.153 - 158 | - |
dc.identifier.wosid | A1996TZ11500019 | - |
dc.date.tcdate | 2018-03-23 | - |
dc.citation.endPage | 158 | - |
dc.citation.number | 2 | - |
dc.citation.startPage | 153 | - |
dc.citation.title | BULLETIN OF THE KOREAN CHEMICAL SOCIETY | - |
dc.citation.volume | 17 | - |
dc.contributor.affiliatedAuthor | Ahn, KH | - |
dc.identifier.scopusid | 2-s2.0-18444416072 | - |
dc.description.journalClass | 1 | - |
dc.description.journalClass | 1 | - |
dc.type.docType | Article | - |
dc.subject.keywordPlus | ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS | - |
dc.subject.keywordPlus | CONJUGATE ADDITION | - |
dc.subject.keywordPlus | ORGANOCOPPER REAGENTS | - |
dc.subject.keywordPlus | ETHERS | - |
dc.subject.keywordPlus | CYCLIZATIONS | - |
dc.subject.keywordPlus | ALKYLATION | - |
dc.subject.keywordPlus | CHEMISTRY | - |
dc.subject.keywordPlus | COMPLEX | - |
dc.subject.keywordPlus | KETONES | - |
dc.subject.keywordPlus | ALKENES | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Chemistry | - |
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