Synthesis and Photochemical Behaviour of 3-(Estran-16-yl)acrylates and 2-(Estran-16-yl)vinyl Ketones†

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Thies Thiemann, Shuntaro Mataka, Masashi Tashiro, Shinya Sasaki and Volkmar Vill


Abstract

C-16-substituted steroids having an unsaturation in the side chain have been synthesized by sequential Arnold–Vilsmeier and Wittig reactions, subsequent photochemical studies showing the formation of either a dimeric structure or the occurrence of E/Z-isomerization; for one example, treatment with H2 over Pd–C led to full reduction of the side-chain and ring D.


References

  1. Cf.A. Makriyannis, D.-P. Yang and T. Mavromoustakos, The Molecular Features of Membrane Perturbation by Anaesthetic Steroids, in Steroids and Neuronal Activity, Ciba Foundation Symposium 153, Wiley, Chichester 1990, p. 172 and references cited therein Search PubMed.
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  3. (a) Z. Arnold and A. Holy, Collect. Czech. Chem. Commun., 1962, 27, 2886 Search PubMed.
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