Abstract
Epimeric 17-acetoxy-17-ethynylandrost-4-en-3-ones react with diacetoxyiodobenzene and iodine in acetic acid or methanol in an unusual manner to give 17-acetoxy-21,21-diiodo-17-pregn-4-en-3,20-diones, which are then converted to 21-monoiodides and 21-acetates. Epimeric 17-hydroxy-17-ethynylandrost-4-en-3-ones are inert under these conditions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. M. Turuta, T. M. Fadeeva, A. V. Kamernitskii, and Lu Dyk Chi, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2810 (1989).
A. M. Turuta, T. M. Fadeeva, A. V. Kamernitskii, A. A. Korobov, E. G. Cherepanova, and Lu Dyk Chi, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 675 (1990).
I. Nitta, S. Fujimou, T. Huruyama, S. Inoue, and H. Ueno, Bull. Chem. Soc. Japan,58, 981 (1985).
E. B. Merkushev, L. G. Karnitskaya, G. I. Novosel'tseva, and V. S. Raida, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1153 (1978).
E. B. Merkushev, Usp. Khim.,56, No. 9, 1444 (1987).
K. Aoki and Y. Ogata, Bull. Soc. Chem. Japan,41, 1476 (1968).
Y. Ogata and I. Urasaki, J. Org. Chem.,36, 2164 (1971).
J. C. Danilewicz and W. Klyne, J. Chem. Soc., No. 12, 4950 (1962).
Japanese Patent No. 15, 998 (C 07J 5/00); Chem. Abstr.,98, 198603p (1983).
E. M. Chen, R. M. Klefer, and L. J. Andrews, J. Am. Chem. Soc.,89, 428 (1967).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2875–2878, December, 1991.
Rights and permissions
About this article
Cite this article
Turuta, A.M., Vesela, I.V., Kamernitskii, A.V. et al. Transformed steroids. 186. Use of the diacetoxyiodobenzeneiodine system for the conversion of epimeric 17-ethynylandrost-4-en-17-ol-3-ones to pregnanes. Russ Chem Bull 40, 2508–2511 (1991). https://doi.org/10.1007/BF00959734
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00959734