Stoner Eric J, Allen Michael S, Christesen Alan C, Henry Rodger F, Hollis L Steven, Keyes Robert, Marsden Ian, Rehm Tamara C, Shiroor Sandeep G, Soni Niru B, Stewart Kent D
Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064-6290, USA.
J Org Chem. 2005 Apr 15;70(8):3332-5. doi: 10.1021/jo0500131.
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.
