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Note | Regular issue | Vol 75, No. 5, 2008, pp.1233-1239
Published online, 22nd January, 2008
DOI: 10.3987/COM-07-11308
Unexpected Unique Behavior of Spiro-Isoquinolines with a Cyclohexadienone System in Attempted Dienone-Phenol Rearrangement

Hiroki Shigehisa and Toshio Honda*

*Faculty of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, Japan


8’,9’-Dimethoxy-1’,5’,6’,10b’-tetrahydro-4H-spiro(cyclohexa-2,5- diene-1,2’-pyrrolo[2,1-a]isoquinoline)-3’,4-dione 2 with a basic skeleton of a natural product, annnosqualine, exhibited unique behavior in a dienone-phenol rearrangement. Treatment of 2 with trifluoroacetic acid gave a simple 1-benzylisoquinoline alkaloid, norarmepavine 4. Plausible reaction mechanism for the observed transformation is also described.