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  • Title: An unusual intramolecular hetero-Diels-Alder cycloaddition.
    Author: Stoner EJ, Allen MS, Christesen AC, Henry RF, Hollis LS, Keyes R, Marsden I, Rehm TC, Shiroor SG, Soni NB, Stewart KD.
    Journal: J Org Chem; 2005 Apr 15; 70(8):3332-5. PubMed ID: 15823010.
    Abstract:
    A new reaction of erythronolides, an intramolecular hetero-Diels-Alder, has been discovered. Heated aqueous alcoholic solutions of ABT-773 (1) and its cis isomer (3) convert slowly to cycloadducts 2 and 4, respectively. Optimal reaction conditions, mechanistic studies supported by molecular modeling, and biological activity data are reported. Single-crystal X-ray structures for both adducts 2 and 4 have been obtained.
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