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Total synthesis of (±)-heliannuol C and E via aromatic Claisen rearrangement |
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| Authors: | James R. Vyvyan Jennifer M. Oaksmith Bevin W. Parks Elaine M. Peterson |
| Affiliation: | Department of Chemistry, Western Washington University, Bellingham, WA 98225, USA |
| Abstract: | The total synthesis of heliannuol C and E from a common intermediate are described. Key steps in the synthesis include a regioselective aromatic Claisen rearrangement to install the (1-vinyl)-4-methyl-3-pentenyl substituent and regioselective biomimetic 7-endo and 6-exo phenol epoxide cyclizations to form the cyclic ether moieties. |
| Keywords: | Allelopathy Biomimetic reactions Epoxides Herbicides Oxygen heterocycles |
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