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Synthesis
DOI: 10.1055/a-2714-9838
Paper

Biosynthetic approach towards Drimentines and Indotertines: Study of acid promoted transformation of 3a-prenylpyrroloindolines

Authors

  • Kazuhiro Higuchi 

    1   Pharmaceutical sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Ayumu Tanabe

    1   Pharmaceutical sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Daichi Honma

    1   Pharmaceutical sciences, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Motoki Ito

    2   Chemistry of Functional Molecules, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)

  • Shigeo Sugiyama

    2   Chemistry of Functional Molecules, Meiji Pharmaceutical University, Kiyose, Japan (Ringgold ID: RIN34779)
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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.



Publication History

Received: 30 August 2025

Accepted after revision: 01 October 2025

Accepted Manuscript online:
01 October 2025

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