Abstract
The reaction of grossmisin (8α-hydroxyachillin,1) with chlorine in benzene afforded a mixture of products. The less polar product readily crystallized after chromatography. According to the X-ray diffraction data, this product has the structure of 1α,10β-dichloro-1,10-dihydrogrossmisin. The second chloro derivative of grossmisin,viz., 8β-chloroachillin, was prepared in good yield by the reaction of lactone1 with PCl5 in CHCl3 in the presence of Py.
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References
K. C. Engvild,Phytochemistry, 1986,25, 781.
A. G. Berdin, C. M. Adekenov, V. A. Raldugin, M. M. Shakirov, A. G. Druganov, A. T. Kulyyasov, and G. A. Tolstikov,Izv. Akad. Nauk. Ser. Khim. 1999, 2010 [Russ. Chem. Bull., 1999,48, 1987 (Engl. Transl.)].
O. V. Alebastrov, V. A. Raldugin, M. M. Shakirov, I. Yu. Bagryanskaya, Yu. V. Gatilov, A. T. Kulyyasov, C. M. Adekenov, and G. A. Tolstikov,Izv. Akad. Nauk. Ser. Khim., 2000, 1635 [Russ. Chem. Bull., Int. Ed., 2000,49, 1624 (Engl. Transl.)].
S. M. Adekenov, N. M. Gafurov, A. Zh. Turmukhambetov, and V. I. Ivlev,Khim. Prirod Soedin., 1987, 305 [Chem. Nat. Comp., 1987 (Engl. Transl.)]
A. D. Kagarlitskii, S. M. Adekenov, and A. N. Kupriyanov,Seskviterpenovye laktony rastenii Tsentral'nogo Kazakhstana [Sesquiterpene Lactones from Plants of Central Kazakhstan], Izd-vo Nauka Kaz. SSR. Alma-Ata, 1987, 240 pp. (in Russian).
H. Takyanagi, H. Ogura, and T. B. H. McMurry,Chem. Pharm. Bull., 1990,38, 581.
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor,J. Chem. Soc., Perkin Trans 2, 1987, SI.
Yu. V. Zefirov and P. M. Zorkii,Zh. Strukt. Khim., 1976,17, 994, [J. Struct. Chem., (USSR), 1976,17 (Engl. Transl.)].
C. K. Ingold,Structure and Mechanism in Organic Chemistry, Cornell University Press, New York, Ithaca, 1969.
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Published inIzvestiya Akademii Nauk Seriya Khimicheskaya, No. 11, pp. 1932–1934, November, 2000.
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Alebastrov, O.V., Pigiltsova, S.A., Atazhanova, G.A. et al. Synthesis of two new chloro derivatives of the guaianolide grossmisin and the crystal structure of one derivative. Russ Chem Bull 49, 1902–1904 (2000). https://doi.org/10.1007/BF02494933
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DOI: https://doi.org/10.1007/BF02494933