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

Kazuhiro Higuchi; Ayumu Tanabe; Daichi Honma; Motoki Ito; Shigeo Sugiyama

doi:10.1055/a-2714-9838

Synthesis, Table of Contents

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

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

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

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

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

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

Abstract

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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.

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