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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 8: 2521 - 2526

DOI: https://doi.org/10.6023/cjoc202203040

ARTICLES

Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate

  • Ran Gao ,
  • Weisheng Tian
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  • a School of Chemistry and Materials Science, Huaibei Normal University, Huaibei, Anhui 235000
    b Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences, Shanghai 200032
* E-mail: ;

Received date: 2022-03-21

  Revised date: 2022-04-27

  Online published: 2022-05-07

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Abstract

Azedarachol (3) and 2α,3α,20R-trihydroxypregnane-16β-methacrylate (4) were isolated from the root bark of Melia azedarach L. in 1984 by Nakatani and coworkers. Azedarachol (3) shows excellent antifeedant activity against the larvae of Ajrotis sejetum Denis at the concentration of 500 μg/mL, and 2α,3α,20R-trihydroxypregnane-16β-methacrylate (4) inhibits the HGC27 tumor cells with an IC50 value of (11.3±0.5) μg/mL. The noteworthy activities and the high oxidation state structure as well as the scarce of sample suppling in nature resources have attracted considerable attention from the synthetic community. Herein the synthesis of these two natural products from preganetriol (2) is reported. The route features a stereoselective inversion at C(20) and a substrate controlled dihydroxylation of C(23) double bond. 3 and 4 were obtained in an overall yields of 6% (11 steps) and 7.5% (11 steps), respectively.

Key words： preganetriol; azedarachol; 2α,3α,20R-trihydroxypregnane-16β-methacrylate; total synthesis; natural products

Cite this article

Ran Gao , Weisheng Tian . Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2521 -2526 . DOI: 10.6023/cjoc202203040

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Compound 10/11 cannot be separated by column chromatography, and the proportion of oxidation product 10a/11a obtained by further oxidation is 74%/11%.
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