Stereoselective Substrate‐Controlled Asymmetric Syntheses of both 2,5‐cis‐ and 2,5‐trans‐Tetrahydrofuranoid Oxylipids: Stereodivergent Intramolecular Amide Enolate Alkylation |
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Authors: | Hongjun Jang Iljin Shin Prof?Dr Dongjoo Lee Prof?Dr Hyoungsu Kim Prof?Dr Deukjoon Kim |
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Institution: | 1. College of Pharmacy, Ajou University, Suwon, Korea;2. College of Pharmacy, Seoul National University, Seoul, Korea |
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Abstract: | The concise, highly stereoselective, substrate‐controlled asymmetric total syntheses of both 2,5‐cis‐ and 2,5‐trans‐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 C3‐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. |
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Keywords: | alkylations cyclizations heterocycles natural products total synthesis |
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