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有机化学
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有机化学 ›› 2005, Vol. 25 ›› Issue (12): 1556-1559. 上一篇    下一篇

研究论文

6-亚甲基-17α-乙酰氧基-18-甲基-19-失碳-孕甾-4-烯-3,20-二酮的合成新方法研究

寻国良，廖清江*   

  1. (中国药科大学药学院 南京210009)
  • 收稿日期:2004-12-28 修回日期:2005-06-17 发布日期:2005-11-30
  • 通讯作者: 廖清江

New Synthetic Method of 16-Methylene-17α-acetoxy-18-methyl- 19-norpregn-4-ene-3,20-dione

XUN Guo-Liang, LIAO Qing-Jiang*   

  1. (Pharmacy College, China Pharmaceutical University, Nanjing 210009)
  • Received:2004-12-28 Revised:2005-06-17 Published:2005-11-30
  • Contact: LIAO Qing-Jiang

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报道了16-亚甲基-17α-乙酰氧基-18-甲基-19-失碳-孕甾-4-烯-3,20-二酮的新合成方法. 以左旋18-甲基炔诺酮为原料, 通过脱水、氧化、环合、热解、环氧化、开环氧环、水解七步反应合成了目标化合物, 总收率20.0%. 其中化合物12, 13, 14, 15, 16尚未见文献报道.

关键词: 16-亚甲基-17α-乙酰氧基-18-甲基-19-失碳-孕甾-4-烯-3,20-二酮, 左旋18-甲基炔诺酮, 合成新方法

16-Methylene-17α-acetoxy-18-methyl-19-norpregn-4-ene-3,20-dione was synthesized by using levonorgestrel as staring material, via a 7 step process including dehydration, oxidation, cyclization, ther-molysis, epoxidation, epoxy-ring opening and hydrolysis. The chemical structure of the target compound was confirmed by IR, 1H NMR, MS spectra and elemental analysis. With a total yield of 20.0%, the new steroids 12, 13, 14, 15 and 16 were never reported.

Key words: 16-methylene-17α-acetoxy-18-methyl-19-norpregn-4-ene-3,20-dione, new synthetic method, levonorgestrel