Novel photoisomerization of 1-acylindoles to 3-acylindolenines. General entry to the total synthesis of Strychnos and Aspidosperma alkaloids

Y Ban, K Yoshida, J Goto, T Oishi

Index: Ban, Yoshio; Yoshida, Kiyoshi; Goto, Jiro; Oishi, Takeshi Journal of the American Chemical Society, 1981 , vol. 103, # 23 p. 6990 - 6992

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Citation Number: 58

Abstract

Meanwhile, photoisomerizations of 1-acylindoles of an enamide system have been described to merely provide 3-, 4-, and 6-acylindoles by the usual photo-Fries type of rearrar~ gement.~ In this communication, we report the novel photorearrangement synchronized with a conversion of 1-acylindoles la-d to 3-acylindolenines 2a-d, as depicted in Scheme I, which, with R'= CH2CH2NHR2, n= 2, 3, was followed by a simultaneous ...