Scopine

Scopine

Scopine

Chemical compound

Scopine is a tropane alkaloid found in a variety of plants including Mandragora root,[2] Senecio mikanioides (Delairea odorata),[3] Scopolia carniolica,[4] and Scopolia lurida.[5]

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Scopine can be prepared by the hydrolysis of scopolamine.[1][6][7] 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.[8]

See also

References

  1. [1]
    Werner, Gottfried; Schmidt, K.-H. (1967). "Die darstellung von scopin aus scopolamin". Tetrahedron Letters. 8 (14): 1283–1284. doi:10.1016/S0040-4039(00)90685-3. PMID 6044210.
  2. [2]
    Staub, H. (1962). "The chemical constituents of the Mandragora root. II. The alkaloids". Helvetica Chimica Acta. 45 (7): 2297–2305. doi:10.1002/hlca.19620450703.
  3. [3]
    Adams, Roger; Gianturco, Maurizio (1957). "Senecio alkaloids: mikanoidine, the alkaloid from Senecio mikanoides". Journal of the American Chemical Society. 79: 166–169. doi:10.1021/ja01558a045.
  4. [4]
    Bendik, I.; Bauerova, O.; Bauer, S.; Mokry, J.; Tomko, J. (1958). "Alkaloids from Scopolia carniolica". Chemicke Zvesti. 12: 181–184.
  5. [5]
    Szymanska, Miroslawa (1967). "Alkaloids in Scopolia lurida. Chromatographic analysis. Isolation of cuscohygrine". Acta Poloniae Pharmaceutica. 24 (1): 59–64.
  6. [6]
    Meinwald, J.; Chapman, O. L. (1957). "Alkaline hydrolysis of scopolamine methoxymethochloride: a new route to scopine". Journal of the American Chemical Society. 79 (3): 665–666. doi:10.1021/ja01560a042.
  7. [7]
    Willstatter, Richard; Berner, Endre (1923). "Hydrolysis of scopolamine". Berichte der Deutschen Chemischen Gesellschaft B. 56 (5): 1079–1082. doi:10.1002/cber.19230560515.
  8. [8]
    Hayakawa, Y.; Baba, Y.; Makino, S.; Noyori, R. (1978). "Carbon-carbon bond formation promoted by transition metal carbonyls. 19. General synthesis of tropane alkaloids via the polybromo ketone-iron carbonyl reaction". J. Am. Chem. Soc. 100 (6): 1786–1791. doi:10.1021/ja00474a021.
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