42 8,13a-プロパノベルビン誘導体の反応

抄録

Acetoneberberine type enamine (2) gave 8,13a-propanoberbine derivatives on the following three reactions; a) oxidation of (2) with potassium permanganate, b) annelation via (2) as intermediate on the treatment of protoberberine type alkaloids with acetone in the presence of alkali, and c) alkylation of (2) with alkyl halide. The structures of 8,13a-propanoberbine derivatives were deduced from chemical and spectral data. Acidic hydrolysis of 8,13a-propanoberbine derivatives, Hofmann degradation product (24), and possible mechanism for this intramolecular cyclization of acetonyl group of (2) are discussed. The analysis of mass spectra of 8,13a-propanoberbine derivatives leading to find a characteristic fragmentation pattern is also discussed.