Browse

Total Syntheses of Wondonins and Isowondonins Based on a Biosynthetic Pathway
생합성 예상 경로를 기반으로 한 Wondonins과 Isowondonins의 전합성

DC Field Value Language
dc.contributor.advisor김상희-
dc.contributor.authorShuaiYu-
dc.date.accessioned2017-07-13T16:39:15Z-
dc.date.available2019-11-06-
dc.date.issued2016-08-
dc.identifier.other000000136266-
dc.identifier.urihttps://hdl.handle.net/10371/120142-
dc.description학위논문 (박사)-- 서울대학교 대학원 : 약학과, 2016. 8. 김상희.-
dc.description.abstractThe first total syntheses of wondonins and isowondonins, which are unusual imidazole marine alkaloids, has been accomplished through the development of methods for the selective formation of styryl sulfate group and regioselective alkylation of the imidazole. Application of the Noyori asymmetric hydrogenation of ketones allows the asymmetric synthesis of isowondonins. These results in conjunction with ECD calculations led to the determination of the absolute configuration of isowondonins.-
dc.description.tableofcontents1.Introduction 1

2.Results and Discussion 5

3.Conclusion 14

4.Experimental Section 15
4.1 Synthesis of (±)-wondonin A (1) and B (2) 16
4.2 Synthesis of (±)-isowondonin A (3) and (±)-isowondonin B (4) 30
4.3 Synthesis of (-)-isowondonin A (3) and (-)-isowondonin B (4) 31
4.4 Synthesis of (+)-28a and (+)-28b 40
4.5 Study of the selective formation of styryl sulfate 43
4.6 Data comparison between natural and synthetic (±)-wondonin A (1), (±)-wodonin B (2(-)-isowondonin A (3) and (-)-isowondonin B (4) 44
4.7 Absolute configuration determination of the stereogenic center at C2 50
4.8 Chiral HPLC chromatograms of (-)-27a and (-)-27b 56
4.9 Calculation of the nucleophilicity of the amine 57
4.10 Determine absolute configuration using ECD analysis 62

5.Reference 68

Appendix. Spectra of Compounds 72

국문 초록 101
-
dc.formatapplication/pdf-
dc.format.extent7211253 bytes-
dc.format.mediumapplication/pdf-
dc.language.isoen-
dc.publisher서울대학교 대학원-
dc.subjectAngiogenesis-
dc.subjectE/Z-Selective styryl sulfate formation-
dc.subjectRegioselective imidazole alkylation-
dc.subjectNoyori asymmetric hydrogenation-
dc.subjectTotal synthesis-
dc.subject.ddc615-
dc.titleTotal Syntheses of Wondonins and Isowondonins Based on a Biosynthetic Pathway-
dc.title.alternative생합성 예상 경로를 기반으로 한 Wondonins과 Isowondonins의 전합성-
dc.typeThesis-
dc.contributor.AlternativeAuthor于帅-
dc.description.degreeDoctor-
dc.citation.pages101-
dc.contributor.affiliation약학대학 약학과-
dc.date.awarded2016-08-
Appears in Collections:
College of Pharmacy (약학대학)Dept. of Pharmacy (약학과)Theses (Ph.D. / Sc.D._약학과)
Files in This Item:
  • mendeley

Items in S-Space are protected by copyright, with all rights reserved, unless otherwise indicated.

Browse