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Stereoselective Total Syntheses of both (+)-2,5-cis- and (+)-2,5-trans- Tetrahydrofuranoid Oxylipids
- Alternative Title
- HongJun Jang
- Author(s)
- 장홍준
- Alternative Author(s)
- HongJun Jang
- Advisor
- 김형수
- Department
- 일반대학원 약학과
- Publisher
- The Graduate School, Ajou University
- Publication Year
- 2020-02
- Language
- eng
- Alternative Abstract
- The concise, highly stereoselective, substrate-controlled asymmetric total syntheses of both 2,5-trans- and 2,5-cis-tetrahydrofuranoid nematocidal oxylipids from the Australian brown algae Notheia anomala have been accomplished in a stereodivergent fashion. The highly stereoselective intramolecular amide enolate alkylation strategy provides access to both stereoisomers of the 3-hydroxy-2,5- disubstituted tetrahydrofuran core of these marine natural products through chelate and nonchelate control, which is driven by the C(3)-hydroxy protecting group. This approach offers an optional and highly stereoelective access to any of the eight possible stereoisomers of the 2,5-disubstituted-3-oxygenated tetrahydrofuran skeleton, an important structural feature which is present in many biologically active natural products.
- Fulltext
- Appears in Collections:
- Graduate School of Ajou University > Department of Pharmacy > 4. Theses(Ph.D)
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