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A New Synthetic Route Towards Picealactone a from an Abietic Acid

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Chemistry of Natural Compounds Aims and scope

A new synthetic route towards picealactone A from an abietic acid, dehydroabietic acid, was introduced in this study. In this synthetic route, the picealactone A was synthesized by a tandem oxide/intramolecular esterification of 7-carbonyl dehydroabietic acid catalyzed by Yb(OTf)3.

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References

  1. S. Savluchinske Feio, L. Nunes, P. Tavares Pereira, A. M. Silva, J. C. Roseiro, B. Gigante, and M. J. Marcelo-Curto, J. Microbiol. Methods, 70, 465 (2007)

    Article  CAS  PubMed  Google Scholar 

  2. I. A. Tolmacheva, A. V. Tarantin, A. A. Boteva, L. V. Anikina, Y. B. Vikharev, V. V. Grishko, and A. G. Tolstikov, Pharm. Chem. J., 40, 489 (2006).

    Article  CAS  Google Scholar 

  3. R. Tanaka, H. Tokuda, and Y. Ezaki, Phytomedicine, 15, 985 (2008).

    Article  CAS  PubMed  Google Scholar 

  4. X. P. Rao, Z. Q. Song, L. He, and W. H. Jia, Chem. Pharm. Bull., 56, 1575 (2008).

    Article  CAS  PubMed  Google Scholar 

  5. T. Ohwada, T. Nonomura, K. Maki, K. Sakamoto, S. Ohya, K. Muraki, and Y. Imaizumi, Bioorg. Med. Chem. Lett., 13, 3971 (2003).

    Article  CAS  PubMed  Google Scholar 

  6. T. Tashima, Y. Toriumi, Y. Mochizuki, T. Nonomura, S. Nagaoka, K. Furukawa, H. Tsuru, S. Adachi-Akahane, and T. Ohwada, Bioorg. Med. Chem., 14, 8014 (2006).

    Article  CAS  PubMed  Google Scholar 

  7. Y. M. Cui, E. Yasutomi, Y. Otani, T. Yoshinaga, K. Ido, K. Sawada, M. Kawahata, K. Yamaguchi, and T. Ohwada, Bioorg. Med. Chem. Lett., 18, 6386 (2008).

    Article  CAS  PubMed  Google Scholar 

  8. Y. M. Cui, E. Yasutomi, Y. Otani, K. Ido, T. Yoshinaga, K. Sawada, and T. Ohwada, Bioorg. Med. Chem., 18, 8642 (2010).

    Article  CAS  PubMed  Google Scholar 

  9. G. Gessner, Y. M. Cui, Y. Otani, T. Ohwada, M. Soom, T. Hoshi, and S. H. Heinemann, Proc. Natl. Acad. Sci. USA, 109, 3552 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Y. H. Kuo, M. H. Yeh, and H. C. Lin, Chem. Pharm. Bull., 52, 861 (2004).

    Article  CAS  PubMed  Google Scholar 

  11. E. J. Alvarez-Manzaneda, R. Chahboun, J. J. Guardia, M. Lachkar, A. Dahdouh, A. Lara, and I. Messouri, Tetrahedron Lett., 47, 2577 (2006).

    Article  CAS  Google Scholar 

  12. E. J. Alvarez-Manzaneda, R. Chahboun, E. Cabrera, E. Alvarez, R. Alvarez-Manzaneda, M. Lachkarc, and I. Messouric, Tetrahedron Lett., 48, 989 (2007).

    Article  CAS  Google Scholar 

  13. N. J. Halbrook and R. V. Lawrence, J. Org. Chem., 31, 4246 (1966).

    Article  CAS  Google Scholar 

  14. X. S. Lv, Y. M. Cui, H. Y. Wang, H. X. Lin, and W. Y. Ni, Chin. Chem. Lett., 24, 1023 (2013).

    Article  CAS  Google Scholar 

  15. M. Curini, F. Epifano, S. Genovese, M. C. Marcotullio, and O. Rosati, Org. Lett., 7, 1331 (2005).

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

This work was supported by the National Natural Science Foundation of China under Grant U1202265; National Natural Science Foundation of China under Grant 31500487; International Science and technology cooperation under Grant 2014DFR31300.

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Authors and Affiliations

  1. Institute of Chemical Industry of Forest Products, China Academy of Forestry; National Engineering Laboratory for Biomass Chemical Utilization; State Forestry Administrations Key and Open Laboratory for Forest Chemical Engineering; Jiangsu Provincial Key Laboratory for Biomass Energy and Material, 210042, Nanjing, Jiangsu, P. R. China

    Shengliang Liao, Minggui Shen, Shibin Shang, Xiaoping Rao & Zhanqian Song

  2. Institute of New Technology of Forestry, China Academy of Forestry, 100091, Beijing, P. R. China

    Minggui Shen, Shibin Shang & Xiaoping Rao

  3. Department of Chemistry and Biochemistry, University of Michigan-Flint, 303E Kearsley Street, Flint, MI, 48502, USA

    Jie Song

Authors
  1. Shengliang Liao
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  2. Minggui Shen
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  3. Jie Song
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  4. Shibin Shang
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  5. Xiaoping Rao
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  6. Zhanqian Song
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Corresponding authors

Correspondence to Minggui Shen or Zhanqian Song.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2017, pp. 560–561.

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Liao, S., Shen, M., Song, J. et al. A New Synthetic Route Towards Picealactone a from an Abietic Acid. Chem Nat Compd 53, 658–660 (2017). https://doi.org/10.1007/s10600-017-2084-2

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  • DOI: https://doi.org/10.1007/s10600-017-2084-2

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