Construction of the Akuammiline Alkaloid Core Structure via Stereoselective E-Ring Formation.
Naoki HashimotoJunichi TaguchiTakumi KasagiNorihito ArichiShinsuke InukiHiroaki OhnoPublished in: The Journal of organic chemistry (2024)
Construction of the core structure of akuammiline alkaloids with three-dimensional cage-like structures for their diversity-oriented synthesis was investigated. Extensive exploration centered around the introduction of nitrogen functional groups and construction of the E-ring in an intramolecular or intermolecular manner revealed that a Claisen rearrangement approach involving intramolecular amination provided a common precursor, potentially facilitating divergent access to various types of akuammiline alkaloids.