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Paper | Special issue | Vol 99, No. 1, 2019, pp.379-388
Published online, 14th September, 2018
DOI: 10.3987/COM-18-S(F)30
Biomimetic Synthesis of Iheyamine A from Spirocyclic Oxindoles

Takumi Abe,* Syuhei Satake, and Koji Yamada*

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

Abstract

The biomimetic synthesis of azepinobisindole alkaloid iheyamine A from a spirocyclic oxindole via an oxidative rearrangement has been accomplished for the first time. Furthermore, an unprecedented method for constructing 2,1’-spirocyclic oxindoles from azepinobisindoles through an alternative oxidative rearrangement has been explored.