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Stereochemistry of Tropine and pseudo-Tropine

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Abstract

ACYL migration N → O was used for the determination of the configuration of the diastereomeric 1.2-amino-alcohols, for example, ephedrine1, chloromycetin2, as well as for that of the alicyclic amino-alcohols (2-amino-cyclohexanol and pentanols) containing flexible3a or rigid3b ring systems by Fodor and Kiss. More recently, McCasland4 elucidated the configuration of the epimeric inosamines by the same means.

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References

  1. Fodor, G., et al., (a) J. Org. Chem., 14, 337 (1949); (b) ibid., 15, 226 (1950).

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  2. Fodor, G., Kiss, J., and Sallay, I., J. Chem. Soc., 1858 (1951).

  3. Fodor, G., and Kiss, J., (a) Nature, 164, 917 (1949); (b) Research, 4, 382 (1951); (c) Research, 4, 381 (1951).

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  4. McCasland, J. Amer. Chem. Soc., 73, 2295 (1951).

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  5. (a) Willstätter, R., and Bode, A., Ber., 33, 416 (1900). (b) Gadamer, J., Arch. Pharm., 239, 298 (1901). (c) Barrowcliff, M., and Tutin, F., J. Chem. Soc., 95, 1967 (1909). (d) Willstätter, R., and Bommer, M., Lieb. Ann., 422, 18 (1921).

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  6. (a) Kimura, K. K., and Unna, K. R., J. Pharmacol. Exp. Therap., 98, 286 (1950). (b) Issekutz, Sen., B., and Nádor, K., meeting of the Hungarian Society for Physiology at Szeged, June 1950.

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  7. Prepared by Polonovsky, M., and Polonovski, M., Bull. Soc. Chim., 39, 1147 (1926), who suggested it had the structure of an acyl-amide salt; our electrometric titrations proved the correctness of this assumption.

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Authors and Affiliations

  1. Institute of Organic Chemistry, University, Szeged,

    G. FODOR & K. NÁDOR

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  1. G. FODOR
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  2. K. NÁDOR
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FODOR, G., NÁDOR, K. Stereochemistry of Tropine and pseudo-Tropine. Nature 169, 462–463 (1952). https://doi.org/10.1038/169462a0

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