Solid-phase synthesis of macrocyclic systems by a cyclorelease strategy: Application of the stille coupling to a synthesis of (S)-zearalenone

Angewandte Chemie - International Edition

Volumn 37, Issue 18, 1998, Pages 2534-2537

  Nicolaou, K C ^a,b   Winssinger, Nicolas ^a,b   Pastor, Joaquin ^a,b   Murphy, Fiona ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cyclizations; Natural products; Solid phase synthesis; Stille coupling; Synthetic methods

Indexed keywords

EID: 0032476095     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981002)37:18<2534::AID-ANIE2534>3.0.CO;2-F     Document Type: Article

References (41)

1. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
2. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
3. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
4. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
5. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
6. For reviews, see: a) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. 1996, 108, 2436-2487; Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337; b) L. A. Thompson, J. A. Ellman, Chem. Rev. 1996, 96, 555-617; c) M. A. Gallop, R. W. Barret, W. J. Dower, S. P. Foder, E. M. Gorden, J. Med. Chem. 1994, 37 1233-1281; d) E. M. Gorden, R. M. Barret, W. J. Dower, S. P. Foder, M. A. Gallop, ibid. 1994, 37, 1385-1405; e) W. H. Moos, G. D. Green, M. R. Pavia, Annu. Rep. Med. Chem. 1993, 28, 315-324.
7. For general references, see: a) J. J. Baldwin, I. Henderson in Synthesis of Encoded Small Molecule Combinatorial Libraries (Ed.: J. P. Delvin), Dekker, New York, NY, 1997; b) A. W. Czarnick, Curr. Opin. Chem. Biol. 1997, 1, 60-66; c) X. Y. Xiao, C. Zhao, H. Potash, M. P. Nova, Angew. Chem. 1997, 109, 799-801; Angew. Chem. Int. Ed. Engl. 1997, 56, 780-782.
8. For general references, see: a) J. J. Baldwin, I. Henderson in Synthesis of Encoded Small Molecule Combinatorial Libraries (Ed.: J. P. Delvin), Dekker, New York, NY, 1997; b) A. W. Czarnick, Curr. Opin. Chem. Biol. 1997, 1, 60-66; c) X. Y. Xiao, C. Zhao, H. Potash, M. P. Nova, Angew. Chem. 1997, 109, 799-801; Angew. Chem. Int. Ed. Engl. 1997, 56, 780-782.
9. For general references, see: a) J. J. Baldwin, I. Henderson in Synthesis of Encoded Small Molecule Combinatorial Libraries (Ed.: J. P. Delvin), Dekker, New York, NY, 1997; b) A. W. Czarnick, Curr. Opin. Chem. Biol. 1997, 1, 60-66; c) X. Y. Xiao, C. Zhao, H. Potash, M. P. Nova, Angew. Chem. 1997, 109, 799-801; Angew. Chem. Int. Ed. Engl. 1997, 56, 780-782.
10. For general references, see: a) J. J. Baldwin, I. Henderson in Synthesis of Encoded Small Molecule Combinatorial Libraries (Ed.: J. P. Delvin), Dekker, New York, NY, 1997; b) A. W. Czarnick, Curr. Opin. Chem. Biol. 1997, 1, 60-66; c) X. Y. Xiao, C. Zhao, H. Potash, M. P. Nova, Angew. Chem. 1997, 109, 799-801; Angew. Chem. Int. Ed. Engl. 1997, 56, 780-782.
11. For references relating to non-oligomeric natural product synthesis on solid phase, see: a) K. C. Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarbia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272; b) S. Chen. K. D. Janda, J. Am. Chem. Soc. 1997, 119, 8724-8725.
12. For references relating to non-oligomeric natural product synthesis on solid phase, see: a) K. C. Nicolaou, N. Winssinger, J. Pastor, S. Ninkovic, F. Sarbia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272; b) S. Chen. K. D. Janda, J. Am. Chem. Soc. 1997, 119, 8724-8725.
13. For previous examples of cyclorelease, see: a) X. Beebe, N. E. Schore, M. J. Kurth, J. Am. Chem. Soc. 1992, 114, 10061-10062; b) S. H. Dewitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. R. Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913. For carbon-carbon bond cyclorelease, see: c) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252; d) A. D. Piscopio, J. F. Miller, K. Koch, ibid. 1997, 38, 7143-7146; reference [3a]; e) M. R. Gowravaram, M. A. Gallop, ibid. 1997, 38, 6973-6976.
14. For previous examples of cyclorelease, see: a) X. Beebe, N. E. Schore, M. J. Kurth, J. Am. Chem. Soc. 1992, 114, 10061-10062; b) S. H. Dewitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. R. Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913. For carbon-carbon bond cyclorelease, see: c) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252; d) A. D. Piscopio, J. F. Miller, K. Koch, ibid. 1997, 38, 7143-7146; reference [3a]; e) M. R. Gowravaram, M. A. Gallop, ibid. 1997, 38, 6973-6976.
15. For previous examples of cyclorelease, see: a) X. Beebe, N. E. Schore, M. J. Kurth, J. Am. Chem. Soc. 1992, 114, 10061-10062; b) S. H. Dewitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. R. Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913. For carbon-carbon bond cyclorelease, see: c) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252; d) A. D. Piscopio, J. F. Miller, K. Koch, ibid. 1997, 38, 7143-7146; reference [3a]; e) M. R. Gowravaram, M. A. Gallop, ibid. 1997, 38, 6973-6976.
16. For previous examples of cyclorelease, see: a) X. Beebe, N. E. Schore, M. J. Kurth, J. Am. Chem. Soc. 1992, 114, 10061-10062; b) S. H. Dewitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. R. Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913. For carbon-carbon bond cyclorelease, see: c) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252; d) A. D. Piscopio, J. F. Miller, K. Koch, ibid. 1997, 38, 7143-7146; reference [3a]; e) M. R. Gowravaram, M. A. Gallop, ibid. 1997, 38, 6973-6976.
17. For previous examples of cyclorelease, see: a) X. Beebe, N. E. Schore, M. J. Kurth, J. Am. Chem. Soc. 1992, 114, 10061-10062; b) S. H. Dewitt, J. S. Kiely, C. J. Stankovic, M. C. Schroeder, D. M. R. Cody, M. R. Pavia, Proc. Natl. Acad. Sci. USA 1993, 90, 6909-6913. For carbon-carbon bond cyclorelease, see: c) J. H. van Maarseveen, J. A. J. den Hartog, V. Engelen, E. Finner, G. Visser, C. G. Kruse, Tetrahedron Lett. 1996, 37, 8249-8252; d) A. D. Piscopio, J. F. Miller, K. Koch, ibid. 1997, 38, 7143-7146; reference [3a]; e) M. R. Gowravaram, M. A. Gallop, ibid. 1997, 38, 6973-6976.
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32. While the preparation of polymer-supported organotin reagents 3 and 4 have been reported on a macroporous resin by Neumann et al., the authors were unsuccessful in their attempts to prepare it on a 2% cross-linked resin: a) M. Peterseim. W. P. Neumann, React. Polym. 1993, 20, 189-205; b) U. Gerigk, M. Gerlach, W. P. Neumann, R. Vieler, V. Weintritt, Synthesis 1990, 448-452. For some applications of polymer supported organotin reagents, see: H. Kuhn, W. P. Neumann, Synlett 1994, 123-124; and M. Gerlach, F. Jordens, H. Kuhn, W. P. Neumann, M. Peterseim, J. Org. Chem. 1991, 56, 5971-5972.
33. While the preparation of polymer-supported organotin reagents 3 and 4 have been reported on a macroporous resin by Neumann et al., the authors were unsuccessful in their attempts to prepare it on a 2% cross-linked resin: a) M. Peterseim. W. P. Neumann, React. Polym. 1993, 20, 189-205; b) U. Gerigk, M. Gerlach, W. P. Neumann, R. Vieler, V. Weintritt, Synthesis 1990, 448-452. For some applications of polymer supported organotin reagents, see: H. Kuhn, W. P. Neumann, Synlett 1994, 123-124; and M. Gerlach, F. Jordens, H. Kuhn, W. P. Neumann, M. Peterseim, J. Org. Chem. 1991, 56, 5971-5972.
34. While the preparation of polymer-supported organotin reagents 3 and 4 have been reported on a macroporous resin by Neumann et al., the authors were unsuccessful in their attempts to prepare it on a 2% cross-linked resin: a) M. Peterseim. W. P. Neumann, React. Polym. 1993, 20, 189-205; b) U. Gerigk, M. Gerlach, W. P. Neumann, R. Vieler, V. Weintritt, Synthesis 1990, 448-452. For some applications of polymer supported organotin reagents, see: H. Kuhn, W. P. Neumann, Synlett 1994, 123-124; and M. Gerlach, F. Jordens, H. Kuhn, W. P. Neumann, M. Peterseim, J. Org. Chem. 1991, 56, 5971-5972.
35. While the preparation of polymer-supported organotin reagents 3 and 4 have been reported on a macroporous resin by Neumann et al., the authors were unsuccessful in their attempts to prepare it on a 2% cross-linked resin: a) M. Peterseim. W. P. Neumann, React. Polym. 1993, 20, 189-205; b) U. Gerigk, M. Gerlach, W. P. Neumann, R. Vieler, V. Weintritt, Synthesis 1990, 448-452. For some applications of polymer supported organotin reagents, see: H. Kuhn, W. P. Neumann, Synlett 1994, 123-124; and M. Gerlach, F. Jordens, H. Kuhn, W. P. Neumann, M. Peterseim, J. Org. Chem. 1991, 56, 5971-5972.
36. 3.
37. W. P. Neumann, J. Pedain, Tetrahedron Lett. 1964, 2461-2465.
38. The yield was calculated based on the mass gain of the polymer. All subsequent yields are based on the amount of compound recovered upon iodonolysis from the resin.
39. The ratios of polymer bound vinyl tin isomers were extrapolated from the ratio of vinyl iodide isomers obtained upon iodonolysis.
40. 3.
41. [6]