Unexpected unique behavior of spiro-isoquinolines with a cyclohexadienone system in attempted dienone-phenol rearrangement.

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

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