Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1, 3, 4-oxadiazole
SE Wolkenberg, DL Boger
Index: Wilkie, Gordon D.; Elliott, Gregory I.; Blagg, Brian S. J.; Wolkenberg, Scott E.; Soenen, Danielle R.; Miller, Michael M.; Pollack, Scott; Boger, Dale L. Journal of the American Chemical Society, 2002 , vol. 124, # 38 p. 11292 - 11294
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Citation Number: 65
Abstract
Although a limited number of reports describe the cycloaddition reactivity of electron-deficient 1,3,4-oxadiazoles, they typically employ symmetrical oxadiazoles bearing strongly electron-withdrawing substituents (CF 3 , SO 2 Et, CO 2 Me) in intermolecular reactions. 10 Reactions with olefinic dienophiles proceed through an initial [4 + 2] cycloadduct that undergoes a loss of N 2 to generate a carbonyl ylide, which reacts further with the olefins in a 1,3-dipolar cycloaddition (Figure ...