Synthesis and reactions of 3,7-cycloerythrinans: Skeletal rearrangement of 2,7,8-trioxoerythrinans to 4-oxo-4H-pyrido[2,1-a]isoquinolines

DOI: 10.1248/cpb.39.1402

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1402 - 1406 (1991)

Update date:2022-08-03

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Authors:

Tsuda Tsuda

Sakai Sakai

Sano Sano

Toda Toda

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Article abstract of DOI:10.1248/cpb.39.1402

Treatment of 2,7,8-trioxoerythrinan derivatives with anhydrous phosphoric acid or Lewis acids gave 3,7-cycloerythrinan derivatives via an intramolecular aldol condensation. The structures of the products were established by spectroscopic and chemical means. Further treatment of the 3,7-cycloerythrinans with anhydrous phosphoric acid resulted in skeletal rearrangement to yield 6,7-dihydro-4-oxo-4H-pyrido[2,1-a]isoquinolines, whose structures were also determined mainly by spectroscopic means.

Full text of DOI:10.1248/cpb.39.1402

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