Ring closing metathesis as an efficient approach to branched cyclitols and aminocyclitols: A short synthesis of valiolamine

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 853-856

  Sellier, Odile ^a   Van de Weghe, Pierre ^a   Le Nouen, Didier ^a   Strehler, Christiane ^a   Eustache, Jacques ^a  

^a Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXENE DERIVATIVE; VALIOLAMINE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033613678     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02539-8     Document Type: Article

References (24)

1. For a recent review on the application of RCM to the synthesis of macrocycles see : Fürstner, A.; Langemann, K. Synthesis 1997, 792-803.
2. See also : (a) Nicolaou, K.C.; He, Y.; Vourloumis, D.; Vallberg, H.; Roschangar, F.; Sarabia, F.; Ninkovic, S.; Yang, Z.; Trujillo, J.I. J.Am.Chem.Soc. 1997, 119, 7960-7973.
3. (b) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E.J.; Danishefsky, S.J. J.Am.Chem.Soc. 1997, 119, 10073-10092.
4. For examples of preparations of medium carbo- and heterocycles, see : (a) Crimmins, M.T. Choy, A.L. J.Org.Chem. 1997, 62, 7548-7549.
5. (b) Schmalz, H-G. Angew. Chem. Int. Ed. Engl. 1995, 34, 1833-1836.
6. Applications in the area of sugar chemistry have recently been published : Ovaa, H.; Leeuwenburgh, M.A.; Overkleeft, H.S.; van der Marel, G.A. van Boom, J.H. Tetrahedron Lett. 1998, 39, 3025-3028.
7. While this manuscript was being prepared, application of RCM to the synthesis of an unsaturated, 5-membered aminocyclitol has been published : Ovaa, H.; Codée, J.D.C.; Lastdrager, B.; Overkleeft, H.S.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett. 1998, 39, 7987-7990.
8. (a) Aoyagi, T.; Yamamoto, T.; Kojiri, K.; Morisha, H.; Nagai, M.; Hamada, M.; Takeuchi, T.; Umezawa, H. J.Antibiot. 1989, 42, 883-889;
9. (b) Morishima, H.; Kojiri, K.; Yamamoto, T.; Aoyagi, T.; Nakamura, H.; Litaka, Y J.Antibiot. 1989, 42, 1008-1011.
10. (a)Ando, O.; Satake, H.; Itoi, K.; Sato, A.; Nakajima, M.; Takahashi, S.; Haruyama, H. J.Antibiot. 1991, 44, 1165-1168;
11. (b) Ando, O.; Nakajima, M.; Hamano, K.; Itoi, K. J.Antibiot. 1993, 46, 1116-1125.
12. Kameda, Y.; Asano, N.; Yoshikawa, M.; Takeuchi, M.; Yamaguchi, T.; Matsui, K. J.Antibiot. 1984, 37, 130-1307.
13. Shing, T.K.M.; Wan, L.H. J.Org.Chem. 1996, 61, 8468-8479.
14. Suami, T.; Ogawa, S. Adv. in Carbohydr. Chem. Biochem. 1990, 48, 21-90.
15. MsComsey, D.F.; Maryanoff, B.E. J.Org.Chem. 1994, 59, 2652-2654.
16. Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J.Med.Chem. 1986, 29, 1038-1046.
17. Fukase, H.; Horii, S. J.Org.Chem. 1992, 57, 3651-3658.
18. Freeman, F.; Robarge, R.D. Carbohydr.Res. 1986, 154, 270-274.
19. (a) Nguyen, S.T.; Grubbs, R.H. J.Am.Chem.Soc. 1993, 115, 9858-9859;
20. 2, Ru catalyst : 20 mol %) affording a 42% yield of the 7 + 8 mixture.
21. Schrock, R.R.; Murdzek, J.S.; Bazan, G.C.; Robbins, G.C.; DiMare, M.; O'Regan, M. J.Am.Chem.Soc. 1990, 112, 3875-3886.
22. Hollards, R.; Becher, D.; Gaudemer, A.; Polonsky, J. Tetrahedron 1968, 24, 1633-1646.
23. 2O, 250MHz) δ 1.68 (1H, dd, J = 15, 4 Hz), 1.88 (1H, dd, J = 15, 3 Hz), 3.34 (1H, ddd, J = 9.5, 4, 3 Hz), 3.41(1H, d, J = 9.5 Hz), 3.48 (2H, ABq, J = 11.5 Hz), 3.57 ( 1H, dd, J = 4, 10 Hz), 3.83 (1H, t, J = 9.5 Hz).
24. 6