Ring opening cross-metathesis on solid support: A combinatorial library synthesis of highly functionalized cyclopentanes

Molecular Diversity

Volumn 3, Issue 3, 1997, Pages 173-179

  Cao, Jingrong ^a   Cuny, Gregory D ^a   Hauske, James R ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

Cyclopentanes; Ring opening cross methathesis; Ruthenium; Solid support

Indexed keywords

CYCLOPENTANE DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FACTUAL DATABASE; MASS SPECTROMETRY; METHODOLOGY; ORGANIC CHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CHEMISTRY, ORGANIC; CYCLOPENTANES; DATABASES, FACTUAL; INDICATORS AND REAGENTS; MASS SPECTROMETRY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0031615757     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1009663720800     Document Type: Article

References (30)

1. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
2. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
3. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
4. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
5. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
6. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
7. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
8. Reviews: a. Grubbs, R.H., Miller, S.J. and Fu, G.C., Ring-closing metathesis and related processes in organic synthesis, Acc. Chem. Res., 28 (1995) 446-452. b. Schmalz, H.-G., Catalytic ring-closing metathesis: A new, powerful technique for carbon-carbon coupling in organic synthesis, Angew. Chem. Int. Ed. Engl., 34 (1995) 1833-1836. Cross-Metathesis: c. Brümmer, O., Rückert, A. and Bletchert, S., Olefin cross-metathesis with monosubstituted olefins, Chem. Eur. J., 3 (1997) 441-446. d. Crowe, W.E., Goldberg, D.R. and Zhang, Z. J., Preparation of allylsilanes via cross-metathesis, Tetrahedron Lett., 37 (1996) 2117-2120. e. Crowe, W.E. and Zhang, Z.J., Highly selective cross-metathesis of terminal olefins, J. Am. Chem. Soc., 115 (1993) 10998-10999. f. Crowe, W.E. and Goldberg, D.R., Acrylonitrile cross-metathesis: coaxing olefin metathesis reactivity from a reluctant substrate, J. Am. Chem. Soc., 117 (1995) 5162-5163. Tandem ROM-RCM: g. Zuercher, W.J., Hashimoto, M. and Grubbs, R.H., Tandem ring opening-ring closing metathesis of cyclic olefins, J. Am. Chem. Soc., 118 (1996) 6634-6640. Rearrangements: Harrity, J.P.A., Visser, M.S., Gleason, J.D. and Hoveyda, A.H., Ru-catalyzed rearrangement of styrenyl ethers. enantioselective synthesis of chromenes through Zr-and Ru-catalyzed processes, J. Am. Chem. Soc., 119 (1997) 1488-1489.
9. a. Fürstner, A. and Langemann, K., Conformationally unbiased macrocyclization reactions by ring closing metathesis, J. Org. Chem., 61 (1996) 3942-3943.
10. b. Kim, S.-H., Zuercher, J., Bowden, N. B. and Grubbs, R.H., Catalytic ring closing metathesis of dienynes: construction of fused bicydo [n.m.0] rings, J. Org. Chem., 61 (1996), 1073-1081.
11. c. Kinoshita, A. and Mori, M., Total synthesis of (-)-stemoamide using ruthenium-catalyzed enyne metathesis reaction, J. Org. Chem., 61 (1996) 8356-8357.
12. a. Schuster, M., Pernerstorfer, J. and Blechert, S., Ruthenium-catalyzed metathesis of polymer-bound olefins, Angew. Chem. Int. Ed. Engl., 35 (1996) 1979-1980.
13. b. Nicolaou, K.C., Winssinger, N., Pastor, J., Ninkovic, S., Sarabia, F., He, Y., Vourloumis, D., Yang, Z., Li, T., Giannakakou, P. and Hamel, E., Synthesis of epothilones A and B in solid and solution phase, Nature, 387 (1997) 268-272.
14. e. van Maarseveen, J.H., den Hartog, J.A.J., Engelen, V., Finner, E., Visser, G., Kruse, C. G., Solid phase ring-closing metathesis: cyclization/cleavage approach and towards a seven membered cycloolefin, Tetrahedron Lett., 37 (1996) 8249-8252.
15. d. Miller, J.F., Termin, A., Koch, K. and Piscopio, A.D., An ester enolate claisen/ring closing metathesis route to functionalized carbocycles and heterocycles, Presented at the 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997; paper ORGN 064.
16. a. Cuny, G.D., Cao, J. and Hauske, J.R., Ring opening cross-metathesis on solid support, Tetrahedron Lett., 38 (1997) 5237-5240.
17. b. Cuny, G.D., Cao, J. and Hauske, J.R., Ring opening cross-metathesis on solid support, Presented at the 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997; paper ORGN 571.
18. c. Snapper, M.L., Tallarico, J.A. and Randell, M.L., Regio-and stereoselective ring-opening cross-metathesis. Rapid entry into functionalized bicyclo[6.3.0] ring systems, J. Am. Chem. Soc., 119 (1997) 1478-1479.
19. d. Schneider, M.F., Lucas, N., Velder, J. and Blechert, S., Selective ring-opening olefin metathesis of functionalized monosubstituted olefins, Angew. Chem. Int. Ed. Engl., 36 (1997) 257-259.
20. e. Randall, M.L., Tallarico, J.A. and Snapper, M.L., Selective ring-opening cross-metathesis. Short synthesis of multifidene and viridiene, J. Am. Chem. Soc., 117 (1995) 9610-9611.
21. f. Schneider, M.F. and Blechert, S., Synthesis of highly substituted cyclopentane and tetrahydrofuran derivatives by cross olefin metathesis, Angew. Chem. Int. Ed. Engl., 35 (1996) 411-412.
22. g. We have also demonstrated solid-phase ROM with other bicyclic olefins, including 7-oxabicyclo[2.2.1]hept-2-ene and 2-azabicyclo[2.2.1]hept-5-en-3-one derivatives.
23. 2] and its reactions, Angew. Chem. Int. Ed. Engl., 34 (1995) 2039-2041.
24. 2: The influence of the alkylidene moiety on metathesis activity, J. Am. Chem. Soc., 118 (1996) 100-110.
25. c. Commercially available from Strem Chemicals, Inc., Newburyport, MA, U.S.A.
26. Balkenhohl, F., von dem Bussche-Hünnefeld, C., Lansky, A. and Zechel, C., Combinatorial synthesis of small organic molecules, Angew. Chem. Int. Ed. Engl., 35 (1996) 2289-2337.
27. Hauske, J.R. and Dorff, P., A Solid phase CBZ chloride equivalent- a new matrix specific linker, Tetrahedron Lett., 36 (1995) 1589-1592.
28. Coste, J., Dufour, M.-N., Pantaloni, A. and Castro, B., BROP: A new reagent for coupling N-methylated amino acids, Tetrahedron Lett., 31 (1990) 669-672.
29. Mukaiyama, T, Yamashita, H. and Asami, M., An asymmetric synthesis of bicyclic lactones and its application to the asymmetric synthesis of (1R, 3S)-cis-chrysanthemic acid, Chem. Lett., (1983) 385-388.
30. Shon, Y.-S, Lee and T.R., Catalytic ring-closing olefin metathesis of sulfur-containing species: heteroatom and other effects, Tetrahedron Lett., 38 (1997) 1283-1286.