A stereoselective synthesis of natural (+)-caparratriene was developed starting from commercially available L-menthol and tiglic aldehyde. The key step was a Wittig reaction of the latter with the triphenylphosphorane generated from (R)-(–)-citronellyl bromide. (+)-Caparratriene as a mixture (4:1) of 2E,4E- and 2E,4Z-stereoisomers is a known anticancer agent.
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References
E. Palomino, C. Maldonado, M. B. Kempff, and M. B. Ksebati, J. Nat. Prod., 59, 77 (1996).
J. R. Vyvyan, E. A. Peterson, and M. L. Stephan, Tetrahedron Lett., 40, 4947 (1999).
P. Das and J. McNulty, Tetrahedron Lett., 51, 3197 (2010).
G. Yu. Ishmuratov, M. P. Yakovleva, V. A. Ganieva, R. R. Muslukhov, and G. A. Tolstikov, Chem. Nat. Compd., 41, 41 (2005).
M. D. Tzirakis, M. N. Alberti, and M. Orfanopoulos, Org. Lett., 13, 3364 (2011).
S. Sankaranarayanan and S. Chattopadhyay, Tetrahedron: Asymmetry, 9, 2627 (1998).
M. Miyashita, A. Yoshikoshi, and P. A. Grieco, J. Org. Chem., 42, 3772 (1977).
Y. Tanaka, H. Honda, K. Ohsawa, and I. Yamamoto, J. Pestic. Sci., 14, 197 (1989).
G. Cahiez and M. Alami, Tetrahedron, 45, 4163 (1989).
J. Kim, S. Matsuyama, and T. Suzuki, J. Labelled Compd. Radiopharm., 47, 921 (2004).
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2018, pp. 391–393.
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Vydrina, V.A., Kravchenko, A.A., Yakovleva, M.P. et al. Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde. Chem Nat Compd 54, 461–463 (2018). https://doi.org/10.1007/s10600-018-2379-y
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DOI: https://doi.org/10.1007/s10600-018-2379-y