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(-)-Bisezakyne A 의 전합성과 구조 재교정
| DC Field | Value | Language |
|---|---|---|
| dc.contributor.advisor | 김형수 | - |
| dc.contributor.author | 신일진 | - |
| dc.date.accessioned | 2019-04-01T16:42:37Z | - |
| dc.date.available | 2019-04-01T16:42:37Z | - |
| dc.date.issued | 2019-02 | - |
| dc.identifier.other | 28783 | - |
| dc.identifier.uri | https://dspace.ajou.ac.kr/handle/2018.oak/15240 | - |
| dc.description | 학위논문(박사)--아주대학교 일반대학원 :약학과,2019. 2 | - |
| dc.description.tableofcontents | I. Introduction 1 I.1 Significance of Tetrahydrofuran Skeleton in Nature 1 I.2. Tetrahydrofuran Skeleton in Nature Products 2 I.2.1. Mono-THFs 2 I.2.2. Fused Bis-THFs 5 I.2.3. Adjacent Bis-THFs 6 I.2.4. Non-Adjacent Bis-THFs 8 I.2.5. THF-Containing Macrolides 11 I.2.6. Mono-THF fused with Medium-Sized Ether Ring 14 I.3. Stereoselective Construction of 2,5-Disubstituted THF Skeletons by CarbonCarbon Bond-Forming Cyclization in Total Synthesis of Natural Products 17 I.3.1. Overmans Tandem Prins/Pinacol Reaction for Stereoselective Construction of 2,5-Disubstituted THF Skeletons 20 I.3.2. Lees Radical Reaction for Stereoselective Construction of 2,5-Disubstituted THF Skeletons. 24 II. Results and discussion 33 II.1. Previous Studies 33 II.1.1. Previous Studies On Divergent Construction of 2,5-cis- and 2,5-trans-Disubstituted THFs 33 II.1.2. Previous Results On Divergent Construction of 2,5-cis- and 2,5-trans-Disubstituted THFs by Intramolecular Amide Enolate or Nitrile Anion Alkylation. 34 II.1.3. Protecting Group-Dependent Stereodivergent Intramolecular Amide Enolate Alkylation. 38 II.2. Total Synthesis of Proposed Structure of ()-Bisezakyne A 49 III. Conclusions 72 IV. Experimentals 73 V. References 166 | - |
| dc.language.iso | eng | - |
| dc.publisher | The Graduate School, Ajou University | - |
| dc.rights | 아주대학교 논문은 저작권에 의해 보호받습니다. | - |
| dc.title | (-)-Bisezakyne A 의 전합성과 구조 재교정 | - |
| dc.title.alternative | Iljin Shin | - |
| dc.type | Thesis | - |
| dc.contributor.affiliation | 아주대학교 일반대학원 | - |
| dc.contributor.alternativeName | Iljin Shin | - |
| dc.contributor.department | 일반대학원 약학과 | - |
| dc.date.awarded | 2019. 2 | - |
| dc.description.degree | Doctoral | - |
| dc.identifier.localId | 905149 | - |
| dc.identifier.uci | I804:41038-000000028783 | - |
| dc.identifier.url | http://dcoll.ajou.ac.kr:9080/dcollection/common/orgView/000000028783 | - |
| dc.description.alternativeAbstract | Functionalized tetrahydrofurans (THFs) constitute key structural features of biologically interesting natural products exhibiting significant various pharmacological activities including anticancer, antiviral, antibiotic and antifungal activities (Figure 1). In particular, 2,5-cis- or -trans disubstituted-THFs are found in a wide range of complex natural products which have been largely attracted from synthetic community culminating the development of a number of methodologies. The total synthesis of proposed (−)-bisezakyne A and revised (−)-bisezakyne A have been accomplished in 15 steps for longest sequence from commercially available hexa-1,5-dien-3-ol with an overall yields of 6.8% and 3.7%, respectively. Highlight of the synthesis include the IAEA (intramolecular amide enolate alkylation) for steroselective synthesis of 2,3-cis-2,5-cis-tetrahydrofuran and 2,3-cis-2,5-trans-tetrahydrofuran and the Nakata’s halogenation protocol. In addition, our synthesis unambiguously confirmed the absolute configuration of the natural (−)-bisezakyne A. | - |
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