Asymmetric Total Synthesis of (+)‐Bermudenynol,a C15 Laurencia Metabolite with a Vinyl Chloride Containing Oxocene Skeleton,through Intramolecular Amide Enolate Alkylation |
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| Authors: | Gyudong Kim Dr. Te‐ik Sohn Prof. Dr. Deukjoon Kim Dr. Robert S. Paton |
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| Affiliation: | 1. College of Pharmacy, Seoul National University, Seoul 151‐742 (Korea);2. Chemical Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA (UK) |
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| Abstract: | A substrate‐controlled asymmetric total synthesis of (+)‐bermudenynol, a compact and synthetically challenging C15 Laurencia metabolite that contains several halogen atoms, is reported. The oxocene core, which contains a vinyl chloride, was constructed by an efficient and highly stereoselective intramolecular amide enolate alkylation (IAEA). This result showcases the broad utility of the IAEA methodology as a useful alternative for cases in which the ring‐closing metathesis is inefficient. |
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| Keywords: | intramolecular amide enolate alkylation natural products oxocenes total synthesis |
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