Synthesis of bisindole derivatives using immobilized indolylmetal compounds

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Many biologically active bisindole derivatives have been isolated from natural products. Bisindolylmaleimides are known to show PKC inhibiting activity and a bisindolylbenzoquinone is reported to have an unique insulin-like activity. Some bisindolylpyridines also have cytotoxic activity toward tumor cells. In order to establish a versatile method to synthesize these bisindole derivatives, we investigated solid phase synthesis and fluorous synthesis for these compounds. The use of immobilized indolylboron was found to be effective for the solid phase synthesis and some bisindole derivatives were synthesized. The pseudo dilution effect of polymer support was also found to be effective for the mono coupling of dihalogeno compounds and the sequential coupling strategy was proved to be convenient for the construction of unsymmetrical bisindole structure. Fluorous synthesis was proved to be useful for the separation of fluorous-tagged compounds from non-tagged compounds using fluorous silica gel extraction and a new sulfonyl type tag was developed for the synthesis of tagged bisindoles. A bisindolylbenzoquinone was synthesized using this sulfonyl fluorous tag.