Synthesis of the staurosporine aglycon

CJ Moody, KF Rahimtoola, B Porter…

Index: Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C. Journal of Organic Chemistry, 1992 , vol. 57, # 7 p. 2105 - 2114

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Citation Number: 72

Abstract

A short synthesis of the staurosporine aglycon (6) is reported, the indolocarbazole skeleton being constructed by an intramolecular Diels-Alder reaction followed by a nitrene-mediated ring closure. The synthesis starts by acylation of ethyl indole-2-acetate with oxalyl chloride. The resulting indole-3-glyoxalyl chloride is quenched with 2-nitrocinnamylamine (29) to give the amide (31). Hydrolysis of the ester group and cyclodehydration then gives the ...