Examples of thiylation of natural mono- and bicyclic and variously functionalized monoterpenoids (alkenes, ketones, epoxides, alcohols) and the latest transformation pathways of the newly formed sulfur-containing derivatives were reviewed.
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S. A. Rubtsova, K. S. Rodygin, and A. V. Kuchin, Izv. Komi Nauchn. Tsentra, Ural. Otd., Ross. Akad. Nauk, 18 (2010).
G. Lowe, Tetrahedron, 32, 291 (1976).
I. V. Koval’, Usp. Khim., 62, 813 (1993); 63, 154, 338 (1994).
L. E. Nikitina, O. A. Shkuro, and V. V. Plemenkov, Zh. Org. Khim., 29, 1794 (1993).
W. A. Smit, M. Z. Krimer, and E. A. Vorobeva, Tetrahedron Lett., 16, 2451 (1975).
C. Capozzi, O. De Lucchi, V. Lucchini, and G. Modena, Tetrahedron Lett., 16, 2603 (1975).
M. C. Caserio, C. L. Fisher, and J. K. Kim, J. Org. Chem., 50, 4390 (1985).
C. J. Worrel, US Pat. No. 2,951,874 (1960), Sept. 6, 1960; Ref. Zh. Khim., 17L101 (1961).
I. V. Il’ina, K. P. Volcho, and N. F. Salakhutdinov, Zh. Org. Khim., 44, 11 (2008).
G. A. Tolstikov, F. Ya. Kanzafarov, Yu. A. Sangalov, and U. M. Dzhemilev, Neftekhimiya, 19, 425 (1979).
G. A. Tolstikov, F. Ya. Kanzafarov, U. M. Dzhemilev, R. G. Kantyukova, and L. M. Zelenova, Zh. Org. Khim., 19, 2075 (1983).
V. A. Morgunova, L. E. Nikitina, V. V. Plemenkov, M. G. Fazlyeva, and Yu. V. Chugunov, Zh. Org. Khim., 36, 512 (2000).
G. R. Davletshina, E. Kh. Kazakova, and S. G. Vul’fson, Zh. Org. Khim., 29, 1632 (1993).
L. E. Nikitina, V. A. Startseva, I. A. Vakulenko, and V. V. Plemenkov, Zh. Obshch. Khim., 72, 1041 (2002).
I. V. Kuznetsov, L. E. Nikitina, and V. A. Startseva, Khim. Interesakh Ustoich. Razvit., 19, 217 (2011).
I. S. Nizamov, A. V. Sofronov, I. D. Nizamov, R. A. Cherkasov, and L. E. Nikitina, Zh. Org. Khim., 43, 621 (2007).
A. V. Sofronov, I. S. Nizamov, I. A. Al’metkina, L. E. Nikitina, D. G. Fatykhova, P. V. Zelenikhin, O. N. Il’inskaya, and R. A. Cherkasov, Zh. Obshch. Khim., 80, 1101 (2010).
L. E. Nikitina, V. V. Plemenkov, R. A. Shaikhutdinov, and V. A. Klochkov, Zh. Org. Khim., 32, 1007 (1996).
L. E. Nikitina and V. V. Plemenkov, Chem. Nat. Compd., 26, 530 (1990).
M. Weiwer, X. Chaminade, J. C. Bayon, and E. Dunach, Eur. J. Org. Chem., 2007, 2464 (2007).
A. Gadras, J. Dunogues, R. Calas, and G. Deleris, J. Org. Chem., 49, 442 (1984).
L. E. Nikitina, V. A. Startseva, S. A. Dieva, I. A. Vakulenko, and G. A. Shamov, Chem. Nat. Compd., 42, 178 (2006).
L. E. Nikitina, N. P. Artemova, and V. A. Startseva, Natural and Thio-modified Monoterpenoids [in Russian], Otechestvo, Kazan, 2011, 197 pp.
R. R. Khaliullin and V. V. Plemenkov, Zh. Obshch. Khim., 63, 874 (1993).
L. E. Nikitina, V. V. Plemenkov, A. N. Chernov, I. A. Litivinov, and O. N. Kataeva, Zh. Obshch. Khim., 60, 2303 (1990).
E. S. Izmest’ev, D. V. Sudarikov, S. A. Rubtsova, and A. V. Kuchin, in: Materials of the VIIth All-Russian Conference “Chemistry and Technology of Plant Substances” [in Russian], Syktyvkar, 2011, p. 59.
L. E. Nikitina, N. P. Artemova, and V. A. Startseva, Natural and Thio-modified Monoterpenoids [in Russian], Lap Lambert, Germany, 2012, 167 pp.
A. V. Bodrov, L. E. Nikitina, V. A. Startseva, O. A. Lodochnikova, R. Z. Musin, and O. I. Gnezdilov, Zh. Obshch. Khim., 83, 88 (2013).
D. R. Taylor, Chem. Rev., 67, 317 (1967).
T. L. Jacobs and R. Macomber, J. Org. Chem., 33, 2988 (1968).
L. E. Nikitina, V. V. Plemenkov, V. A. Startseva, S. A. Dieva, and M. S. Baird, Sulfur Lett., 24, 223 (2001).
O. A. Lodochnikova, L. E. Nikitina, V. V. Plemenkov, O. N. Kataeva, I. A. Litvinov, and S. A. Appolonova, Zh. Org. Khim., 35, 248 (1999).
N. V. Zyk, E. K. Beloglazkina, S. E. Sosonyuk, M. N. Bulanov, and Yu. B. Chudinov, Izv. Akad. Nauk, Ser. Khim., 64, 1569 (2000).
F. Akiyama, J. Am. Chem. Soc., 98, 208 (1976).
N. A. Tyukavkina, S. E. Zurabyan, and V. L. Beloborodov, Organic Chemistry. Special Course [in Russian], Drofa, Moscow, 2008, 592 pp.
V. P. Krivonogov, N. G. Afzaletdinova, R. A. Khisamutdinov, L. V. Spirikhin, and Yu. I. Murinov, Zh. Prikl. Khim., 73, 976 (2000).
A. V. Timshina, S. A. Rubtsova, M. I. Kodess, E. G. Matochkina, P. A. Slepukhin, and A. V. Kuchin, Zh. Org. Khim., 44, 1053 (2008).
S. R. Wilson and P. Caldera, J. Org. Chem., 47, 3319 (1982).
N. Deka and J. C. Sarma, Chem. Lett., 30, 794 (2001).
A. V. Timshina, Dissertation, Ural St. Tech. Univ., Syktyvkar, 2009.
K. Tanaka and F. Toda, Chem. Rev., 100, 1025 (2000).
G. Bez and D. Gogoi, Tetrahedron Lett., 47, 5155 (2006).
E. S. Izmestyev, D. V. Sudarikov, S. A. Rubtsova, and A. V. Kuchin, Chem. Nat. Compd. , 47, 46 (2011).
D. J. Protector, N. J. Archer, R. A. Needham, D. Bell, A. P. Marchington, and C. M. Rayner, Tetrahedron, 55, 9611 (1999).
P. N. Kazakov, S. N. Subbotina, S. A. Rubtsova, and A. V. Kuchin, in: Materials of the Vth All-Russian Scientific Seminar “Chemistry and Medicine” [in Russian], Ufa, 2005, p. 29.
R. J. Goodridge, T. W. Hambley, R. K. Haynes, and D. D. Ridley, J. Org. Chem., 53, 2881 (1988).
S. R. Wilson and P. Caldera, J. Org. Chem., 47, 3319 (1982).
S.-W. Chang, C.-Y. Hung, H.-H. Lui, and B.-J. Uang, Tetrahedron: Asymmetry, 9, 521 (1998).
F. Fringuelli, F. Pizzo, and L. Vaccaro, J. Org. Chem., 69, 2315 (2004).
P.-Y. Wu, H.-L. Wu, and B.-J. Uang, J. Org. Chem., 71, 833 (2006).
D. Pandy-Szekeres, G. Deleris, J. P. Picard, J. P. Pillot, and R. Calas, Tetrahedron Lett., 21, 4267 (1980).
A. V. Timshina, S. A. Rubtsova, L. I. Frolova, I. N. Alekseev, P. A. Slepukhin, and A. V. Kuchin, Zh. Org. Khim., 45, 595 (2009).
N. Bakopki, R. V. Palei, and V. V. Plemenkov, Zh. Obshch. Khim., 73, 667 (2003).
E. V. Sirasieva, V. A. Startseva, L. E. Nikitina, I. V. Kuznetsov, and V. V. Klochkov, Chem. Nat. Compd., 42, 693 (2006).
E. V. Sirazieva, V. A. Startseva, L. E. Nikitina, V. V. Plemenkov, V. V. Klochkov, and B. I. Khairutdinov, Chem. Nat. Compd., 40, 478 (2004).
E. V. Sirazieva, Dissertation, Kazan St. Tech. Univ., Kazan, 2006.
A. T. Khan, S. Ghosh, and L. H. Choudhury, Eur. J. Org. Chem., 2006, 2226 (2006).
E. V. Suslov, Dissertation, Inst. Org. Chem., Sib. Br., Russ. Acad. Sci., Novosibirsk, 2009.
M. E. Niyazymbetov, A. L. Laikhter, V. V. Semenov, and D. H. Evans, Tetrahedron Lett., 35, 3037 (1994).
M. K. Hargreaves and L. F. Rabari, Monatsh. Chem., 114, 195 (1983).
P. Bakuzis and M. L. F. Bakuzis, J. Org. Chem., 46, 235 (1981).
E. B. Krein and Z. Aizenshtat, J. Org. Chem., 58, 6103 (1993).
S. Hussain, K. Bharadwaj, M. K. Chaudhuri, and H. Kalita, Eur. J. Org. Chem., 2007, 374 (2007).
R. G. Capon and D. J. Faulkner, J. Am. Chem. Soc., 106, 1819 (1984).
A. Proszenyak, M. Brandvang, C. Charnock, and L. Gundersen, Tetrahedron, 65, 194 (2009).
M. D. Bachi, Y. V. Bilokin, and A. Melman, Tetrahedron Lett., 39, 3035 (1998).
A. Srikrishna and D. Vijaykumar, Tetrahedron Lett., 39, 4901 (1998).
V. A. Morgunova, L. E. Nikitina, V. V. Plemenkov, M. G. Fazlyeva, and Yu. V. Chugunov, Chem. Nat. Compd., 35, 176 (1999).
L. E. Nikitina, V. A. Startseva, V. V. Plemenkov, S. A. Dieva, O. A. Lodochnikova, and I. A. Litvinov, Chem. Nat. Compd., 43, 263 (2007).
J. S. Yadav, B. V. S. Reddy, and G. Baishya, Chem. Lett., 35, 906 (2002).
L. E. Nikitina, I. V. Akulina, R. S. Garaev, N. P. Artemova, L. Yu. Dorofeeva, V. A. Startseva, and E. V. Sirazieva, Pharm. Chem. J., 46, 20 (2007).
L. A. Mukhamedova, M. I. Kudryavtseva, and A. A. Martynov, Izv. Akad. Nauk SSSR, Ser. Khim., 38, 404 (1974).
L. A. Mukhamedova, F. G. Nasybullina, and M. I. Kudryavtseva, Izv. Akad. Nauk SSSR, Ser. Khim., 41, 2066 (1977).
V. A. Startseva, L. E. Nikitina, and V. V. Plemenkov, Zh. Org. Khim., 37, 46 (2001).
L. E. Nikitina, O. A. Shkuro, and V. V. Plemenkov, Chem. Nat. Compd., 30, 223 (1994).
O. A. Lodochnikova, L. E. Nikitina, V. V. Plemenkov, I. A. Litvinov, and O. N. Kataeva, Zh. Obshch. Khim., 68, 1822 (1998).
N. P. Artemova, G. Sh. Bikbulatova, V. V. Plemenkov, I. A. Litvinov, O. N. Kataeva, and V. A. Naumov, Zh. Obshch. Khim., 59, 2718 (1989).
L. E. Nikitina, S. A. Dieva, V. V. Plemenkov, O. A. Lodochnikova, A. T. Gubaidullin, O. N. Kataeva, and I. A. Litvinov, Zh. Obshch. Khim., 71, 1233 (2001).
I. V. Kuznetsov, V. A. Startseva, L. E. Nikitina, and A. V. Bodrov, in: Materials of the VIIIth All-Russian Conference “Chemistry and Medicine” [in Russian], Ufa, 2010, p. 214.
N. P. Artemova, G. Sh. Bikbulatova, V. V. Plemenkov, and Yu. A. Efremov, Zh. Obshch. Khim., 61, 1484 (1991).
I. V. Fedyunina, L. E. Nikitina, and V. V. Plemenkov, Chem. Nat. Compd., 28, 433 (1992); 29, 600 (1993).
I. V. Fedyunina, V. V. Plemenkov, L. E. Nikitina, I. A. Litvinov, and N. Kataeva, Chem. Nat. Compd., 31, 478 (1995).
V. A. Startseva, L. E. Nikitina, N. P. Artemova, S. A. Dieva, and V. V. Plemenkov, Chem. Nat. Compd., 36, 587 (2000).
A. V. Aref’ev, V. A. Startseva, and L. E. Nikitina, Khim. Interesakh Ustoich. Razvit., 249 (2012).
M. Ya. Demakova, Dissertation, Ural. St. Tech. Univ., Ekaterinburg, 2013.
B. P. Bandgar and V. S. Sadavarte, Synlett, 6, 908 (2000).
S. S. Taj and R. Soman, Tetrahedron: Asymmetry, 5, 1513 (1994).
M. Mikolajczyk, W. Perlikowska, and J. Omelanczuk, Synth. Commun., 17, 1009 (1987).
J. M. Blanco, O. Caamano, and F. Fernandez, Tetrahedron, 51, 935 (1995).
W. Perlikowska, M. Gouygou, M. Mikolajczyk, and J. C. Daran, Tetrahedron: Asymmetry, 15, 3519 (2004).
S. V. Pestova, D. V. Sudarikov, S. A. Rubtsova, and A. V. Kutchin, Russ. J. Org. Chem., 49, 366 (2013).
S. S. Taj, A. C. Shah, D. Lee, G. Newton, and R. R. Soman, Tetrahedron: Asymmetry, 6, 1731 (1995).
Y.-M. Tsai, F.-C. Chang, J. Huang, C.-L. Shiu, C.-L. Kao, and J.-S. Liu, Tetrahedron, 53, 4291 (1997).
I. V. Kuznetsov, V. A. Startseva, and L. E. Nikitina, in: Materials of the VIth All-Russian Scientific Seminar “Chemistry and Medicine” [in Russian], Ufa, 2007, p. 179.
S. C. Tsay, L. C. Lin, P. A. Furth, C. C. Shum, D. B. King, S. F. Yu, B. L. Chen, and J. R. Hwu, Synthesis, 25, 329 (1993).
I. A. Vakulenko, V. A. Startseva, L. E. Nikitina, N. P. Artemova, L. L. Frolova, and A. V. Kuchin, Chem. Nat. Compd., 41, 686 (2005).
I. A. Vakulenko, L. E. Nikitina, V. A. Startseva, V. V. Plemenkov, L. L. Frolova, and A. V. Kuchin, in: Materials of the IIIrd All-Russian Conference “Chemistry and Technology of Plant Substances” [in Russian], Saratov, 2004, p. 82.
E. V. Sirazieva, V. A. Startseva, L. E. Nikitina, and A. V. Kalygina, in: Materials of the VIth All-Russian Conference “Chemistry and Technology of Plant Substances” [in Russian], Syktyvkar, 2006, p. 178.
E. V. Sirazieva, V. A. Startseva, L. E. Nikitina, S. A. Lisovskaya, N. I. Glushko, and R. S. Fassakhov, in: Materials of the International Conference “Organic Chemistry from Butlerov and Beilstein to the Present” [in Russian], St. Petersburg, 2006, p. 447.
I. V. Kuznetsov, E. V. Sirazieva, V. A. Startseva, L. E. Nikitina, S. A. Lisovskaya, and N. I. Glushko, in: Materials of the Conference “Synthesis and Promise of Using New Biologically Active Compounds” [in Russian], Kazan, 2007, p. 24.
L. E. Nikitina, V. V. Plemenkov, V. A. Morgunova, V. V. Klochkov, and R. A. Shaikhutdinov, Zh. Org. Khim., 31, 1826 (1995).
F. Chatzopoulos-Ouar and G. Descotes, J.Org. Chem., 50, 118 (1985).
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Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2014, pp. 23–45.
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Ishmuratov, G.Y., Yakovleva, M.P., Tukhvatshin, V.S. et al. Sulfur-Containing Derivatives of Mono- and Bicyclic Natural Monoterpenoids. Chem Nat Compd 50, 22–47 (2014). https://doi.org/10.1007/s10600-014-0862-7
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DOI: https://doi.org/10.1007/s10600-014-0862-7