Abstract
An unusual ring expansion was observed in the course of studies on the synthesis of berberine linked to oligonucleotides at the 13-position. Nitration of oxyberberine (1) gave 13-nitrooxyberberine (2) as the major product. Lithium aluminum hybride reduction of 2 gave ring-expansion product 4 in addition to the expected primary amine 5. The structure of 4, a novel B/C-cis fused ring system, was solved by X-ray crystallography
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