Synthesis of new derivatives of 11-thiolupinine

Journal of Sulfur Chemistry

Volumn 31, Issue 6, 2010, Pages 493-498

  Gueyrard, David ^a   Tlegenov, Rustam T ^b   Steinbruckner, Siegfried ^c   Perly, Bruno ^c   Rollin, Patrick ^d  

^a UNIVERSITÉ LYON 1   (France)

^b Karakalpakstan State University   (Uzbekistan)

^c CEA SACLAY   (France)

^d UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

Hata reaction; Mitsunobu reaction; thioalkaloids; thiofunctionalization; thiolupinine

Indexed keywords

PHOSPHORUS COMPOUNDS;

HATA REACTION; LUPININE; MITSUNOBU REACTIONS; SYNTHESISED; THIOALKALOID; THIOFUNCTIONALIZATION; THIOLUPININE; TYPE METHODS;

REDOX REACTIONS;

EID: 78649776305     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415993.2010.531481     Document Type: Article

References (28)

1. Wrobel, J.T.;Wojtasiewicz, K. In The Alkaloids: Brossi, A., Ed.; Academic: NewYork, 1992; pp 249-297.
2. Matsuda, H.; Morikawa, T.; Oda, M.; Asao,Y.;Yoshikawa, M. Bioorg. Med. Chem. Lett. 2003, 13, 4445-4449;
3. Wang, W.; Oda, T.; Fujita, A.; Mangindaan, R.E.P.; Nakazawa, T.; Ukai, K.; Kobayashi, H.; Namikoshi, M. Tetrahedron 2007, 63, 409-412.
4. LaLonde, R.T.;Wong, C. Pure Appl. Chem. 1977, 49, 169-182.
5. Wink, M. Methods Plant Biochem. 1993, 8, 197-239.
6. Michael, J.P. Nat. Prod. Rep. 2008, 25, 139-165.
7. Novelli, F.; Tasso, B.; Sparatore, F. Il Farmaco 1999, 54, 354-358;
8. Tasso, B.; Sparatore, A.; Sparatore, F. Il Farmaco 2003, 58, 669-676;
9. Sparatore, A.; Novelli, F.; Sparatore, F. Helv. Chim. Acta 2004, 87, 580-591.
10. Novelli, F.; Sparatore, F. Il Farmaco 1993, 48, 1021-1049.
11. Besson, T.; Al Neirabeyeh, M.; Viaud, M.C.; Rollin, P. Synth. Commun. 1990, 20, 1631-1639;
12. Viaud, M.C.; Rollin, P. Synthesis 1990, 130-131;
13. Gueyrard, D.; Lorin, C.; Moravcova, J.; Rollin, P. J. Carbohydr. Chem. 1999, 18, 317-331;
14. Moravcova, J.; Spilova, L.; Capkova, J.; Chéry, F.; Rollin, P. Coll. Czech Chem. Commun. 2000, 65, 1745-1753.
15. Mitsunobu, O. Synthesis 1981, 1-28;
16. Hughes, D.L. Org. Reactions 1992, 42, 335-656.
17. Nakagawa, I.; Aki, K.; Hata, T. J. Chem. Soc., Perkin Trans. 1 1983, 1315-1318.
18. Cleary, D.G. Synth. Commun. 1989, 19, 737-744;
19. Marot, C.; Philipp, C.; Rollin, P. Tetrahedron Lett. 1992, 33, 4575-4578;
20. Takano, S.; Sugihara,Y.; Ogasawara, K. Synlett 1992, 668-670;
21. Cassel, S.; Chaimbault, P.; Lafosse, M.; Lorin, C.; Rollin, P. Sulfur Lett. 1996, 20, 63-70.
22. Dancy, I.; Laupichler, L.; Rollin, P.; Thiem, J. Synlett 1992, 283-284;
23. Dancy, I.; Laupichler, L.; Rollin, P.; Thiem, J. Liebigs Ann. Chem. 1993, 343-350.
24. see, for example, Skaddan, M.B.;W'st, F.R.; Katzenellenbogen, J.A. J. Org. Chem. 1999, 64, 8108-8121.
25. Rollin, P. Tetrahedron Lett. 1986, 27, 4169-4170;
26. (b)Aversa, M.C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. J. Org. Chem. 1999, 64, 2114-2118.
27. Zakharov, V.P.; Aslanov, Kh.A.; Sadykov, A.S.; Ishbaev, A.I. Uzb. Khim. Zh. 1975, 19, 60-64.
28. Tlegenov, R.T.; Pakarinen, J.M.H.; Oresmaa, L.; Ahlgrén, M.; Vainiotalo, P. J. Heterocycl. Chem. 2007, 44, 1339-1344.