Synthesis

Total synthesis of the natural carbazoles murrayanine and murrayafoline A, based on the regioselective Diels-Alder addition of exo-2-oxazolidinone dienes

A Benavides, J Peralta, F Delgado, J Tamariz

文献索引：Benavides, Adriana; Peralta, Javier; Delgado, Francisco; Tamariz, Joaquin Synthesis, 2004 , # 15 p. 2499 - 2504

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被引用次数: 21

摘要

Abstract A new synthesis of the natural carbazoles Murrayanine (1) and Murrayafoline A (3) is described. The key step in the synthetic route involved the regioselective cycloaddition of the diene 4, 5-dimethylene-3-phenyl-1, 3-oxazolidin-2-one (4) to acrolein (6) catalyzed by Lewis acids at low temperature. Direct aromatization of the substituted cyclohexene moiety of adduct 7, and further hydrolysis of the 2-oxazolidinone ring, proved to be a more ...