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Conformational control of bond migration in the D-homo rearrangement of 17-hydroxy-20-keto steroids

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Abstract

The concept of conformational control of bond migration in the trnsition state to theD-homo-annulation of 17-hydroxy-20-keto steroids appears to provide a unified rationale for the observed phenomena.

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References

  1. For leading references see: (a)L. Ruzicka andH. Meldahl, Helv. chim. Acta23, 364 (1940).

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  7. The bond migrations referred to are those involved in producing themajor product of each reaction which in general corresponds to ca. 65% and 100% respectively of the isomer mixtures.

  8. For earlier examples wherein the chair conformation in the transition state of reactions has been invoked to permit a selection of directional course, see:N. L. Wendler, Exper.9, 416 (1953).

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Authors
  1. N. L. Wendler
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  2. D. Taub
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  3. R. Firestone
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Additional information

Contribution from Merck & Co., Inc., Rahway, N. J., presented before the North Jersey Section of the American Chemical Society byN. L. Wendler as part of a lecture entitledStereochemical Effects Attending D-Ring Rearrangements in Steroids, February 3, 1959.

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Wendler, N.L., Taub, D. & Firestone, R. Conformational control of bond migration in the D-homo rearrangement of 17-hydroxy-20-keto steroids. Experientia 15, 237–239 (1959). https://doi.org/10.1007/BF02158127

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  • DOI: https://doi.org/10.1007/BF02158127

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