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Synthesis of hydroxy-γ-sanshool

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Abstract

Hydroxy-γ-sanshool was prepared with 19.5% overall yield through eight steps. Wittig reactions of ylides with ethyl 4-oxobut-2-enoate as well as (2E,4E)-hex-2,4-dienal were key steps to construct a carbon skeleton. The 2E,4Z-isomer in ethyl 8-hydroxyocta-2,4-dienoate can be isomerized to the desired 2E,4E-isomer with iodine as a catalyst, and free tetradeca-2,4,8,10,12-pentaenoic acid can be purified through crystallization in 1% ethyl acetate in n-hexane. The impurities in other intermediates can be easily removed, the synthetic process can avoid the synthesis or use of 4-bromobutyraldehyde which comes from the oxidation of unstable 4-bromobutan-1-ol, and the work-ups were simple.

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References

  1. Yang X (2008) J Agric Food Chem 56:1689

    Article  CAS  Google Scholar 

  2. Ren T, Zhu Y, Xia X, Ding Y, Guo J, Kan J (2017) J Mol Endocrinol 58:113

    Article  CAS  Google Scholar 

  3. Dossou KS, Devkota KP, Morton C, Egan JM, Lu G, Beutler JA, Moaddel R (2013) J Nat Prod 76:2060

    Article  CAS  Google Scholar 

  4. Rong R, Cui MY, Zhang QL, Zhang MY, Yu YM, Zhou XY, Yu ZG, Zhao YL (2016) J Sep Sci 39:2728

    Article  CAS  Google Scholar 

  5. Tokita Y, Yamamoto M, Satoh K, Nishiyama M, Iizuka S, Imamura S, Kase Y (2011) J Pharmacol Sci 115:75

    Article  CAS  Google Scholar 

  6. Aoki K, Igarashi Y, Nishimura H, Morishita I, Usui K (2012) Tetrahedron Lett 53:6000

    Article  CAS  Google Scholar 

  7. Crombie L, Fisher D (1985) Tetrahedron Lett 26:2477

    Article  CAS  Google Scholar 

  8. Crombie L, Fisher D (1985) Tetrahedron Lett 26:2481

    Article  CAS  Google Scholar 

  9. Xia X, Toy PH (2014) Synlett 25:2787

    Article  CAS  Google Scholar 

  10. Zhou J, Xiao Y, Chen T, Gao J, Huang W, Li Z (2020) J Chem Res 1747519820974323

  11. Koley D, Srinivas K, Krishna Y, Gupta A (2014) RSC Adv 4:3934

    Article  CAS  Google Scholar 

  12. Kad GL, Kaur I, Bhandari M, Singh J, Kaur J (2003) Org Process Res Dev 3:339

    Article  Google Scholar 

  13. Khan AA, Kamena F, Timmer MS, Stocker BL (2013) Org Biomol Chem 11:881

    Article  CAS  Google Scholar 

  14. Cloke JB, Pilgrim FJ (1939) J Am Chem Soc 61:2667

    Article  CAS  Google Scholar 

  15. Rigatti R, Ost T, Fashena S (2008) Method for pairwise sequencing of double-stranded DNA on clustered arrays. Patent WO 2008/041002 A2, 2008; (2008) Chem Abstr 148:419098

  16. Leeson PD, Ellis D, Emmett JC (1988) J Med Chem 31:31

    Article  Google Scholar 

  17. Chen X, Zhang Y, Wan H, Wang W, Zhang S (2016) Chem Commun 52:3532

    Article  CAS  Google Scholar 

  18. Cooper SP, Booker-Milburn KI (2015) Angew Chem 127:6596

    Article  Google Scholar 

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Acknowledgements

We thank the State Key Laboratory of Biotherapy, West China Hospital, Sichuan University for 1H NMR, 13C NMR, and HRMS determination. This work was financially supported by the Sichuan Provincial Administration of Traditional Chinese Medicine2018HJZX04.

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Authors and Affiliations

  1. School of Chemical Engineering, Sichuan University, Chengdu, China

    Jiyu Gao, Jianjun Zhou, Taiping Chen, Yan Xiao, Zicheng Li & Wencai Huang

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  1. Jiyu Gao
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  2. Jianjun Zhou
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  3. Taiping Chen
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  4. Yan Xiao
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  5. Zicheng Li
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  6. Wencai Huang
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Correspondence to Zicheng Li.

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Gao, J., Zhou, J., Chen, T. et al. Synthesis of hydroxy-γ-sanshool. Monatsh Chem 152, 545–549 (2021). https://doi.org/10.1007/s00706-021-02762-2

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  • DOI: https://doi.org/10.1007/s00706-021-02762-2

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