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Asymmetric synthesis of valilactone

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Abstract

Total synthesis of (−)-valilactone, an efficient pancreatic lipase inhibitor, was accomplished with the use of Keck allylation in the key step of construction of the target carbon skeleton.

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References

  1. Pommier, A. and Pons, J.-M., Synthesis, 1995, p. 729.

    Google Scholar 

  2. Yang, H.W., Zhao, C., and Romo, D., Tetrahedron, 1997, vol. 53, p. 16 471.

    Article  CAS  Google Scholar 

  3. Yang, H.W. and Romo, D., Tetrahedron, 1999, vol. 55, p. 6403.

    Article  CAS  Google Scholar 

  4. Case-Green, S.C., Davies, S.G., Roberts, P.M., Russell, A.J., and Thomson, J.E., Tetrahedron: Asymmetry, 2008, vol. 19, p. 2620.

    CAS  Google Scholar 

  5. Wu, Y. and Sun, Y.-P., J. Org. Chem., 2006, vol. 71, p. 5748.

    Article  CAS  Google Scholar 

  6. Kitahara, M., Asano, M., Naganawara, H., Maeda, K., Hamada, M., Aoyagi, T., Umezawa, H., Iitaka, Y., and Nakamura, H., J. Antibiot., 1987, vol. 40, p. 1647.

    Article  CAS  Google Scholar 

  7. Bates, R.W., Fernandez-Moro, R., and Ley, S.V., Tetrahedron Lett., 1991, vol. 32, p. 2651.

    Article  CAS  Google Scholar 

  8. Bates, R.W., Fernandez-Moro, R., and Ley, S.V., Tetrahedron, 1991, vol. 47, p. 9929.

    Article  CAS  Google Scholar 

  9. Ma, G., Zancanella, M., Oyola, Y., Richardson, R.D., Smith, J.W., and Romo, D., Org. Lett., 2006, vol. 8, p. 4497.

    Article  CAS  Google Scholar 

  10. Mineeva, I.V. and Kulinkovich, O.G., Russ. J. Org. Chem., 2008, vol. 44, p. 1261.

    Article  CAS  Google Scholar 

  11. Mineyeva, I.V. and Kulinkovich, O.G., Tetrahedron Lett., 2010, vol. 51, p. 1836.

    Article  CAS  Google Scholar 

  12. Mineeva, I.V., Russ. J. Org. Chem., 2012, vol. 48, p. 977.

    Article  CAS  Google Scholar 

  13. Mineeva, I.V., Russ. J. Org. Chem., 2013, vol. 49, p. 712.

    Article  CAS  Google Scholar 

  14. Mineeva, I.V., Russ. J. Org. Chem., 2013, vol. 49, p. 253.

    Article  CAS  Google Scholar 

  15. Keck, G.E. and Yu, T., Org. Lett., 1999, vol. 1, p. 289.

    Article  CAS  Google Scholar 

  16. Sanchez, C.C. and Keck, G.E., Org. Lett., 2005, vol. 7, p. 3053.

    Article  CAS  Google Scholar 

  17. Dale, J.A., Dull, D.L., and Mosher, H.S., J. Org. Chem., 1969, vol. 34, p. 2543.

    Article  CAS  Google Scholar 

  18. Sato, M., Sunami, S., Sugita, Y., and Kaneko, C., Chem. Pharm. Bull., 1994, vol. 42, p. 839.

    Article  CAS  Google Scholar 

  19. Sabitha, G., Srinivas, C., Sudhakar, K., Rajkumar, M., Maruthi, C., and Yadav, J.S., Synthesis, 2007, p. 3886.

    Google Scholar 

  20. Sakaki, J., Sugita, Y., Sato, M., and Kaneko, C., Tetrahedron, 1991, vol. 47, p. 6197.

    Article  CAS  Google Scholar 

  21. Johnson, W.S., Kelson, A.B., and Elliott, J.D., Tetrahedron Lett., 1988, vol. 29, p. 3757.

    Article  CAS  Google Scholar 

  22. Sabitha, G., Sundhakar, K., Srinivas, Ch., and Yadav, J.S., Synthesis, 2007, p. 705.

    Google Scholar 

  23. Soriente, A., De Rosa, M., Villano, R., and Scettri, A., Tetrahedron: Asymmetry, 2000, vol. 11, p. 2255.

    CAS  Google Scholar 

  24. Soriente, A., De Rosa, M., Stanzione, M., Villano, R., and Scettri, A., Tetrahedron: Asymmetry, 2001, vol. 12, p. 959.

    CAS  Google Scholar 

  25. Adam, W., Baeza, J., and Ju-Chao, L., J. Am. Chem. Soc., 1972, vol. 94, p. 2000.

    Article  CAS  Google Scholar 

  26. Ghosh, A.K., Shurrush, K., and Kulkarni, S., J. Org. Chem., 2009, vol. 74, p. 4508.

    Article  CAS  Google Scholar 

  27. Barbier, P. and Schneider, F., Helv. Chim. Acta, 1987, vol. 70, p. 196.

    Article  CAS  Google Scholar 

  28. Muramatsu, I., Murakami, M., Yoneda, T., and Hagiani, A., Bull. Chem. Soc. Jpn., 1965, vol. 38, p. 244.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Belarusian State University, pr. Nezavisimosti 4, Minsk, 220030, Belarus

    I. V. Mineeva

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  1. I. V. Mineeva
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Correspondence to I. V. Mineeva.

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Original Russian Text © I.V. Mineeva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 109–113.

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Mineeva, I.V. Asymmetric synthesis of valilactone. Russ J Org Chem 50, 100–104 (2014). https://doi.org/10.1134/S1070428014010199

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  • DOI: https://doi.org/10.1134/S1070428014010199

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