Isomeric 10-thiopinan-3-ols including (1S,2S,3S,5R)-6,6-dimethyl-2-(sulfanylmethyl)bicyclo[3.1.1]heptan-3-ol were synthesized for the first time from oxygen-containing α- and β-pinene derivatives.
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References
T.-K. Yang, R. Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi, and T.-T. Jong, J. Org. Chem., 59, 914 (1994).
O. De Lucchi, V. Lucchini, C. Marchioro, G. Valle, and G. Modena, J. Org. Chem., 51, 1457 (1986).
R. Kawecki, Tetrahedron: Asymmetry, 10, 4183 (1999).
R. Kawecki, Tetrahedron: Asymmetry, 14, 2827 (2003).
M. A. Umbreit and K. B. Sharpless, J. Am. Chem. Soc., 99, 5526 (1977).
A. Deagostino, P. B. Tivola, C. Prandi, and P. Venturello, J. Chem. Soc. Perkin Trans. 1, 2856 (2001).
K. Mori and Y. Igarashi, Liebigs Ann. Chem., 93 (1988).
E. D. Mihelich and D. J. Eickhoff, J. Org. Chem., 48, 4135 (1983).
G. Zweifel and C. C. Whitney, J. Org. Chem., 31, 4178 (1966).
P. A. Baguley and J. Walton, J. Chem. Soc. Perkin Trans. 1, 2073 (1998).
Z. Rafinski, J. Scianowski, and A. Wojtczak, Lett. Org. Chem., 6, 321 (2009).
R. K. de Richter, M. Bonato, M. Follet, and J. M. Kamenka, J. Org. Chem., 55, 2855 (1990).
Y. Chretien-Bessiere and G. Boussac, Bull. Soc. Chim. Fr., 12, 4728 (1967).
E. Becerra-Martinez, R. Velazquez-Ponce, M. A. Sanchez-Aguilar, A. Rodriguez-Hosteguin, P. Joseph-Nathan, J. Tamariz, and L. G. Zepeda, Tetrahedron: Asymmetry, 18, 2727 (2007).
H. C. Brown, K. J. Murray, L. J. Murray, J. A. Snover, and G. Zweifel, J. Am. Chem. Soc., 82, 4233 (1960).
M. Oba, A. Iwasaki, H. Hitokawa, T. Ikegame, H. Banba, K. Ura, T. Takamura, and K. Nishiyama, Tetrahedron: Asymmetry, 17, 1890 (2006).
J. Scianowski, Z. Rafinski, and A. Wojtczak, Eur. J. Org. Chem., 2006, 3216 (2006).
Acknowledgments
We thank E. N. Zainullina, I. N. Alekseev, and S. P. Kuznetsov, staff members of the Laboratory of Physicochemical Methods Research, Institute of Chemistry, Komi Sci. Cent., UB, RAS for recording and discussing the spectral data. The work was sponsored by the RFBR under scientific project No. 13-03-01312a.
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Translated from Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2015, pp. 231–234.
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Banina, O.A., Sudarikov, D.V., Krymskaya, Y.V. et al. Synthesis of Chiral Hydroxythiols Based on Oxygen-Containing α- and β-Pinene Derivatives. Chem Nat Compd 51, 261–265 (2015). https://doi.org/10.1007/s10600-015-1257-0
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DOI: https://doi.org/10.1007/s10600-015-1257-0