Scopine Explained

Scopine is a tropane alkaloid found in a variety of plants including Mandragora root,^[1] Senecio mikanioides (Delairea odorata),^[2] Scopolia carniolica,^[3] and Scopolia lurida.^[4]

Scopine can be prepared by the hydrolysis of scopolamine.^{[5] [6]} It can also be prepared in three steps from N-methoxycarbonylpyrrole and 1,1,3,3-tetrabromoacetone; the reagents are combined in a [4+3] cycloaddition, followed by a diastereoselective reduction with diisobutylaluminum hydride, and finally a Prilezhaev epoxidation with trifluoroperacetic acid affords scopine.^[7]

See also

• Aposcopolamine
• Umbelliferone

Notes and References

1. Staub, H. . The chemical constituents of the Mandragora root. II. The alkaloids . Helvetica Chimica Acta . 1962 . 45. 2297–2305 . 10.1002/hlca.19620450703 . 7.
2. Adams, Roger . Gianturco, Maurizio . Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides . Journal of the American Chemical Society . 1957 . 79 . 166–169 . 10.1021/ja01558a045.
3. Bendik, I. . Bauerova, O. . Bauer, S. . Mokry, J. . Tomko, J. . Alkaloids from Scopolia carniolica . Chemicke Zvesti . 1958 . 12 . 181–184.
4. Szymanska, Miroslawa . Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine . Acta Poloniae Pharmaceutica . 1967 . 24 . 1 . 59–64.
5. Meinwald, J. . Chapman, O. L. . Alkaline hydrolysis of scopolamine methoxymethochloride: a new route to scopine . Journal of the American Chemical Society . 1957 . 79 . 665–666 . 10.1021/ja01560a042 . 3.
6. Willstatter, Richard . Berner, Endre . Hydrolysis of scopolamine . Berichte der Deutschen Chemischen Gesellschaft B . 1923 . 56 . 1079–1082 . 10.1002/cber.19230560515 . 5.
7. Hayakawa. Y.. Baba. Y.. Makino. S.. Noyori. R.. J. Am. Chem. Soc.. 1978. 100. 6. 1786–1791. Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction. 10.1021/ja00474a021.