ORGN 307 |
A novel approach towards the Agelas alkaloids: intramolecular Diels-Alder reactions of 4-vinylimidazole derivatives
| Yong He, Yingzhong Chen, and Carl J. Lovely. Department of Chemistry and Biochemistry, The University of Texas at Arlington, Box 19065, Arlington, TX 76019 |
| An efficient approach for the construction of the skeleton of the oroidin dimer, ageliferin 1 has been identified which relies on an intramolecular Diels-Alder reaction of a 4-vinylimidazole derivative 2. This thermal [4+2] intramolecular cycloaddition process generates the ABC rings in a single step with the potential for stereocontrol over all three new chiral centers. Recent work has focused on the studies of the steric and electronic effects of the peripheral substituents (R1, R2, R3) on the cyclization reaction. The synthesis and Diels-Alder reactions of these 4-vinylimidazole derivatives 2, along with the synthetic efforts toward the total synthesis of the ageliferin 1 will be presented.  |
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