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Elucidation of Racemization Process of Azaspirene Skeleton in Neutral Aqueous Media
Shun Hirasawa1, Ken Mukai1, Shinnosuke Sakai1
1Department of Chemistry and Biochemistry , Waseda University , 3-4-1 , Ohkubo, Shinjuku-ku , Tokyo 169-8555 , Japan.
Abstract:
Azaspirene and related congeners, which possess various biological activities, have a unique spirocyclic core structure. However, there are few studies on the chemical properties of (-)-azaspirene, despite the fact that it may provide important insights into unveiling the biosynthetic pathway. Here, we report a nine-step chemical synthesis of an azaspirene analogue with a new finding that the natural (-)-azaspirene skeleton easily racemizes in neutral aqueous media.
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