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Synthetic Studies of Madeirolide A: Visible-Light-Induced Radical Cyclization Approach
DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | 이철범 | - |
dc.contributor.author | 황성현 | - |
dc.date.accessioned | 2018-05-28T17:16:15Z | - |
dc.date.available | 2019-04-18 | - |
dc.date.issued | 2018-02 | - |
dc.identifier.other | 000000150877 | - |
dc.identifier.uri | https://hdl.handle.net/10371/141181 | - |
dc.description | 학위논문 (박사)-- 서울대학교 대학원 : 자연과학대학 화학부, 2018. 2. 이철범. | - |
dc.description.abstract | In this thesis, our synthetic efforts toward marine natural product mardeirolide A are described. Madeirolide A is a biologically active polyketide that belongs to a group of macrolides. Madeirolide A have three bicyclic ether units embedded within a stereochemically decorated macrolactone scaffold. The bioactivity and structural complexity make madeirolide A an attractive target for total synthesis. Our approach for the synthesis of madeirolide A is based on the assembly of four fragments – C1-C10 fragment (A ring), C13-C19 fragment (B ring), C20-C27 fragment (C ring), and cinerulose fragment. Constructions of three oxacycles have been carried out through radical cyclization using a visible-light-induced transformation rapidly developed area in the past decade.
Chapter 1 contains the background about madeirolide A, biological activity and structure features. Also, presented briefly are all published synthetic studies. Chapter 2 discusses all of the efforts that have been carried out in the laboratory towards a total synthesis of madeirolde A. | - |
dc.description.tableofcontents | Chapter 1. Marine Macrolide Madeirolide A 1
1.1 Isolation, structure and biological activity 1 1.2 Synthesis of C1-C11 subunit of madeirolide A 3 1.2.1 Patersons approach 3 1.2.2 Carters approach 5 1.3 Reference 7 Chapter 2. Synthetic Studies Toward Madeirolide A 8 2.1 Synthetic plan 8 2.2 Synthesis of C1-C10 subunit, A ring 13 2.2.1 Retrosynthetic analysis 13 2.2.2 Construction of stereogenic centers of 2.31 14 2.2.3 Completion of C1-C10 subunit 17 2.3 Synthesis of C13-C19 subunit, B ring 21 2.3.1 Synthetic plan 21 2.3.2 Substrate synthesis 23 2.3.3 Visible-light-induced radical cyclization of B ring 25 2.3.4 Completion of C13-C19 subunit 27 2.4 Synthesis of C19-C27 subunit, C ring 29 2.4.1 Synthetic plan 29 2.4.2 Substrate synthesis 32 2.4.3 Visible-light-induced radical cyclization of C-ring 33 2.5 Fragments union, Synthesis of C13-C27 subunit 40 2.5.1 Substrate synthesis 40 2.5.2 Michael reaction approach 43 2.5.3 Decarboxylative NHK approach 44 2.5.4 Decarboxylative ketone synthesis 46 2.5.5 Completion of C13-C27 subunit 49 2.6 Conclusion 51 2.7 Reference 52 2.8 Experimental section 55 | - |
dc.format | application/pdf | - |
dc.format.extent | 22109053 bytes | - |
dc.format.medium | application/pdf | - |
dc.language.iso | en | - |
dc.publisher | 서울대학교 대학원 | - |
dc.subject | Madeirolide A | - |
dc.subject | Natural products | - |
dc.subject | Radical cyclization | - |
dc.subject | Photoredox | - |
dc.subject | Total synthesis | - |
dc.subject.ddc | 540 | - |
dc.title | Synthetic Studies of Madeirolide A: Visible-Light-Induced Radical Cyclization Approach | - |
dc.type | Thesis | - |
dc.description.degree | Doctor | - |
dc.contributor.affiliation | 자연과학대학 화학부 | - |
dc.date.awarded | 2018-02 | - |
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