Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids

V.A. Khripach; V.N. Zhabinskii; A.I. Kuchto; G.P. Fando; Y.Y. Zhiburtovich; A.S. Lyakhov; A.A. Govorova; M.B. Groen; J. van der Louw; Æ. de Groot

doi:10.1016/j.steroids.2004.04.006

Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids

V.A. Khripach, V.N. Zhabinskii, A.I. Kuchto, G.P. Fando, Y.Y. Zhiburtovich, A.S. Lyakhov, A.A. Govorova, M.B. Groen, J. van der Louw, Æ. de Groot

Organic Chemistry

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Abstract

The synthesis of 13,14-seco steroids starting from easily available (13S)-13-iodo-6-methoxy-3,5-cyclo-13,14-seco-5-androsta-14,17-dione is described. The C-17 ketone was converted regioselectively into its oxime with simultaneous stereoselective deiodination at C-13. The remaining C-14 carbonyl group was then reduced stereoselectively with Ca(BH4)2. The configurations at the relevant stereocenters of the thus obtained hydroxy oxime were determined by X-ray analysis. Successful regeneration of the C-17 carbonyl group was achieved by treatment of the corresponding oxime acetate with TiCl3.

Original language	English
Pages (from-to)	511-514
Journal	Steroids
Volume	69
Issue number	7
DOIs	https://doi.org/10.1016/j.steroids.2004.04.006
Publication status	Published - 2004

Keywords

medium-sized ring
inactivation
secosteroids
inhibition
mechanism
oxidation

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10.1016/j.steroids.2004.04.006

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Khripach, V. A., Zhabinskii, V. N., Kuchto, A. I., Fando, G. P., Zhiburtovich, Y. Y., Lyakhov, A. S., Govorova, A. A., Groen, M. B., van der Louw, J., & de Groot, Æ. (2004). Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids. Steroids, 69(7), 511-514. https://doi.org/10.1016/j.steroids.2004.04.006

@article{74e025d9b97d4dd89d6f683a855092d9,

title = "Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids",

abstract = "The synthesis of 13,14-seco steroids starting from easily available (13S)-13-iodo-6-methoxy-3,5-cyclo-13,14-seco-5-androsta-14,17-dione is described. The C-17 ketone was converted regioselectively into its oxime with simultaneous stereoselective deiodination at C-13. The remaining C-14 carbonyl group was then reduced stereoselectively with Ca(BH4)2. The configurations at the relevant stereocenters of the thus obtained hydroxy oxime were determined by X-ray analysis. Successful regeneration of the C-17 carbonyl group was achieved by treatment of the corresponding oxime acetate with TiCl3.",

keywords = "medium-sized ring, inactivation, secosteroids, inhibition, mechanism, oxidation",

author = "V.A. Khripach and V.N. Zhabinskii and A.I. Kuchto and G.P. Fando and Y.Y. Zhiburtovich and A.S. Lyakhov and A.A. Govorova and M.B. Groen and \{van der Louw\}, J. and \{de Groot\}, {\AE}.",

year = "2004",

doi = "10.1016/j.steroids.2004.04.006",

language = "English",

volume = "69",

pages = "511--514",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier",

number = "7",

}

Khripach, VA, Zhabinskii, VN, Kuchto, AI, Fando, GP, Zhiburtovich, YY, Lyakhov, AS, Govorova, AA, Groen, MB, van der Louw, J & de Groot, Æ 2004, 'Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids', Steroids, vol. 69, no. 7, pp. 511-514. https://doi.org/10.1016/j.steroids.2004.04.006

TY - JOUR

T1 - Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids

AU - Khripach, V.A.

AU - Zhabinskii, V.N.

AU - Kuchto, A.I.

AU - Fando, G.P.

AU - Zhiburtovich, Y.Y.

AU - Lyakhov, A.S.

AU - Govorova, A.A.

AU - Groen, M.B.

AU - van der Louw, J.

AU - de Groot, Æ.

PY - 2004

Y1 - 2004

N2 - The synthesis of 13,14-seco steroids starting from easily available (13S)-13-iodo-6-methoxy-3,5-cyclo-13,14-seco-5-androsta-14,17-dione is described. The C-17 ketone was converted regioselectively into its oxime with simultaneous stereoselective deiodination at C-13. The remaining C-14 carbonyl group was then reduced stereoselectively with Ca(BH4)2. The configurations at the relevant stereocenters of the thus obtained hydroxy oxime were determined by X-ray analysis. Successful regeneration of the C-17 carbonyl group was achieved by treatment of the corresponding oxime acetate with TiCl3.

AB - The synthesis of 13,14-seco steroids starting from easily available (13S)-13-iodo-6-methoxy-3,5-cyclo-13,14-seco-5-androsta-14,17-dione is described. The C-17 ketone was converted regioselectively into its oxime with simultaneous stereoselective deiodination at C-13. The remaining C-14 carbonyl group was then reduced stereoselectively with Ca(BH4)2. The configurations at the relevant stereocenters of the thus obtained hydroxy oxime were determined by X-ray analysis. Successful regeneration of the C-17 carbonyl group was achieved by treatment of the corresponding oxime acetate with TiCl3.

KW - medium-sized ring

KW - inactivation

KW - secosteroids

KW - inhibition

KW - mechanism

KW - oxidation

U2 - 10.1016/j.steroids.2004.04.006

DO - 10.1016/j.steroids.2004.04.006

M3 - Article

SN - 0039-128X

VL - 69

SP - 511

EP - 514

JO - Steroids

JF - Steroids

IS - 7

ER -

Reaction of (13S)-13-iodo-6beta-methoxy-3alpha,5-cyclo-13,14-seco-5alpha-androstane-14,17-dione with hydroxylamine and its application to the synthesis of new 13,14-seco steroids

Abstract

Keywords

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