The indenobenzazepine-spirobenzylisoquinoline rearrangement; stereocontrolled syntheses of (±)-raddeanine and (±)-yenhusomine |
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Authors: | Gábor Blaskó Natesan Murugesan Alan J Freyer Daniella J Gula Bilge Şener Maurice Shamma |
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Institution: | Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA |
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Abstract: | Stereoselective rearrangement of indenobenzazepine cis ketols and with TPAA in pyridine produces spirobenzylisoquinolines and , respectively. The latter product is also obtained by rearrangement of trans ketol . The transformation of ketols and must, therefore, proceed through the intermediacy of aziridinium cation . A similar process obtains in the transformation of to . NaBH4 reduction of gives (±)-raddeanine (). Rearrangement of diol supplies directly. (±)-Yenhusomine () is obtained from the reamangement of either diol, or . In like fashion, diols and supply spirobenzylisoquinoline . |
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