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Stereochemistry of Cocaine

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Abstract

Two years ago, positive evidence was presented for the configurations of tropin and ψ-tropin1, ψ-ecgonin2, scopolamine and valeroidine3 using the acyl migration reaction4,5 and other methods. Regarding the steric structure of cocaine (I), the cis relationship of the COOH and OH groups has been demonstrated2, while in ψcocaine these groups appear to be trans placed. The failure of N-acetyl-nor-ecgonin ethyl ester to undergo acyl migration was considered2 as evidence for the anti position of both functional groups of (I) with respect to the ring nitrogen atom. However, we tried to get more conclusive experimental proofs; more so since our attention was directed by G. Stork (private communication, October 15, 1952) to the possibility of dehydration during acyl migration in the case of N-acetyl-nor-ecgonine ester. Furthermore, Prof. W. Huckel postulated (January 24, 1953) the hindering effect of the carbethoxyl group to be responsible for the failure of the acyl shift.

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References

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Authors and Affiliations

  1. Institute of Organic Chemistry, University of Szeged,

    G. FODOR, Ö. KOVÁCS & I. WEISZ

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  1. G. FODOR
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  2. Ö. KOVÁCS
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  3. I. WEISZ
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FODOR, G., KOVÁCS, Ö. & WEISZ, I. Stereochemistry of Cocaine. Nature 174, 131–132 (1954). https://doi.org/10.1038/174131a0

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