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Stereoselective asymmetric synthesis and characterization of 17α-acetyoxy-19-nor-progesterone

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Abstract

17α-actoxy-19-nor-progesterone was synthesized by a new efficient stereoselective asymmertric pathway from 19-nor-androst-4-en-3, 17-dione in 5-steps reactions with overall yield 63.3%. Consequently, a strategy was used to produce of 17-α-hydroxyl compound stereoselectively by addition 17-keto steroid with hydrogen cyanide, at the same time, the conditions of this asymmertric reaction were optimized. The titled compound and the intermediate were fully characterized by 1H, one dimension and two dimension 13C-nuclear magnetic resonance, and infrared spectrum. The results show that the rate of 17-α-hydroxyl compound isomeride is sensitively affected by the solution system and the best volume ratio of CH3OH to H2O is 36%. After the carbonyl and hydroxyl groups were protected by ethylenediol and vinyl butyl ether respectively, organometallic addition to CN group with CH3Li, androstance compound was converted to pregnane compound. After removing the protective groups by a mild hydrolytic procedure with high yield, the titled compound was obtained by esterified the above intermidiate. The new pathway gives a good purity of 98% as determined by high performance liquid chromatography.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Hunan University, 410083, Changsha, China

    Tang Rui-ren & Guo Can-cheng (Professor)

  2. School of Chemistry and Chemical Engineering, Central South University, 410083, Changsha, China

    Tang Rui-ren & Fan Bo-lin

Authors
  1. Tang Rui-ren
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  2. Guo Can-cheng
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  3. Fan Bo-lin
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Corresponding author

Correspondence to Guo Can-cheng.

Additional information

Foundation item: Project(20376018) supported by the National Natural Science Foundation of China

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Tang, Rr., Guo, Cc. & Fan, Bl. Stereoselective asymmetric synthesis and characterization of 17α-acetyoxy-19-nor-progesterone. J Cent. South Univ. Technol. 11, 300–303 (2004). https://doi.org/10.1007/s11771-004-0061-y

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  • DOI: https://doi.org/10.1007/s11771-004-0061-y

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