AJOU Central Library Repository: Stereoselective Total Syntheses of both (+)-2,5-cis- and (+)-2,5-trans- Tetrahydrofuranoid Oxylipids

Graduate School of Ajou University Department of Pharmacy 4. Theses(Ph.D)

Stereoselective Total Syntheses of both (+)-2,5-cis- and (+)-2,5-trans- Tetrahydrofuranoid Oxylipids

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.

Appears in Collections:: Graduate School of Ajou University > Department of Pharmacy > 4. Theses(Ph.D)

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