Bicuculline diol

J.D. Phillipson, Phytochemistry, 1977, j 6, 2009). Hypecorin-ine (236, X=0) has been reduced by lithium aluminium hydride to a mixture of bicuculline diol (247, R =0H, R =H) and adlu-mine diol (247, R =H, R =0H), obtained by the reduction of the diastereoisomeric phthalide-isoquinoline alkaloids bicuculline and adlumine (see section 12) with the same reagent (Nonaka and Nishioka, loc.dt.). Hypecorinine has been synthesised from dehydrobicucul1ine by reduction with lithium aluminium hydride and re-oxidation with mercury (II) acetate (B.C. Nall-iah and MacLean, Canad.J.Chem., 1978, 56, 1378). 

From the plant Stylomecon heterophylla, a new alkaloid stylophylline was isolated. Since it is the enantiomer of the already known (— )-)3-hydrastine, it represents (— )-a-hydrastine. Recently, the isolation of (— )-bicuculline from Corydalis severtzovii was reported. The elucidation of the relative and absolute configuration of phthalideisoquinoline alkaloids was independently and simultaneously achieved by several groups of workers (60, 78, 79, 365-368, 419, 540). Although different methods were applied [model compounds, IR, and NMR spectroscopy, pAgo mcs optical rotation, preparation of corresponding diols (type II), 1-benzyl-tetrahydroisoquinoline (VII), and tetrahydroprotoberberine compounds... 

The structure of rhoeagenine (I) suggested that oxidation might give rise to bicuculline or adlumidine (phthalideisoquinoline alkaloids) and that by subsequent correlation the absolute configuration of the rhoeadine and the isorhoeadine series, respectively, could be determined. Reduction would then afford the corresponding diols. However, oxidation and reduction afforded products (430) which did not correspond to phthalideisoquinoline derivatives (see Section III, K). 

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