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Experimental analysis shows acid-promoted transformations of pyrroloindolines, indicating a new synthetic pathway for indotertine derivatives.
To develop a biomimetic synthetic route for bioactive hybrid isoprenoid indotertine and drimentine derivatives, we investigated acid-mediated cyclization/isomerization reactions of 3a-prenyl and 3a-geranyl pyrroloindolines. In the case of the 3a-prenyl derivatives, we discovered a skeletal rearrangement reaction initiated by the opening of pyrrolidine rings. For 3a-geranyl derivatives, we successfully constructed a tetracyclic framework corresponding to the substructure of the indotertines.
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Higuchi et al. (2025) studied this question.
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