C2sc20914d 3170..3174
نویسندگان
چکیده
The pyrroloindoline alkaloids are a structurally diverse family of biologically active natural products, which include compounds such as hodgkinsine (1), naseseazine A (2), and gliocladine C (3) 3 (Fig. 1). As a result of their compelling bioactivities and fascinating structures, this family of alkaloids has been the subject of intense research and has inspired the development of a variety of new synthetic methods to prepare the key heterocyclic ring system. In particular, pyrroloindolines that possess an aryl substituent at C3 (such as 1–3) are uniquely challenging. The current state-of-the-art is Movassaghi and Kim’s recently reported and highly practical Friedel–Crafts type arylation of 3-bromocyclotryptophans, which provides access to C3-aryl pyrroloindolines in two steps from the corresponding tryptophan derivatives. Conceptually, we sought to further streamline the synthesis of C3-aryl pyrroloindolines to a one-step process by developing a transition metal-catalyzed arylative cyclization of tryptamine or tryptophan derivatives, thereby circumventing the need to prepare a brominated intermediate. This type of transformation has been realized by Pd-catalyzed allylation and benzylation processes; however, the corresponding transition metal-catalyzed arylation reactions of tryptamines have remained elusive. Herein, we report a copper-catalyzed arylation of readily available tryptamine derivatives as an operationally simple, direct approach to prepare C3-aryl pyrroloindolines.
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