First total synthesis of the marine illudalane sesquiterpenoid alcyopterosin E

Chemical Communications

Volumn 24, Issue , 2002, Pages 2984-2985

  Witulski, Bernhard ^a   Zimmermann, Axel ^a   Gowans, Nicholas D ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALCYOPTEROSIN E; RHODIUM; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; ENANTIOMER; HUMAN; MOLECULE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; SYNTHESIS;

EID: 0036928830     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b209573d     Document Type: Article

References (27)

1. J. A. Palermo, M. F. Rodríguez Brasco, C. Spagnuolo and A. M. Seldes, J. Org. Chem., 2000, 65, 4482.
2. 4/2 i-PrMgCl, see: R. Tanaka, Y. Nakano, D. Suzuki, H. Urabe and F. Sato, J. Am. Chem. Soc., 2002, 124, 9682.
3. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
4. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
5. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
6. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
7. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
8. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
9. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
10. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
11. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
12. E. Müller, Synthesis, 1974, 761; R. Grigg, R. Scott and P. Stevenson, Tetrahedron Lett., 1982, 23, 2691; R. Grigg, R. Scott and P. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1988, 1357; P. Magnus, D. Witty and A. Stamford, Tetrahedron Lett., 1993, 34, 23; F. E. McDonald, H. Y. H. Zhu and C. R. Holmquist, J. Am. Chem. Soc., 1995, 117, 6605; B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, 2426; R. Grigg, V. Sridharan, J. Wang and J. Xu, Tetrahedron, 2000, 56, 8967; S. Kotha, K. Mohanraja and S. Durani, Chem. Commun., 2000, 1909; B. Witulski, T. Stengel and J. M. Fernández-Hernández, Chem. Commun., 2000, 1965; F. E. McDonald and V. Smolentsev, Org. Lett., 2002, 4, 745.
13. Pterosin Z and calomelanolactone: S. J. Neeson and P. J. Stevenson, Tetrahedron, 1989, 45, 6239.
14. Clausine C and the marine carbazole alkaloid hyellazole: B. Witulski and C. Alayrac, Angew. Chem., Int. Ed., 2002, 41, 3281.
15. (S)-3-n-butylphtalide: B. Witulski and A. Zimmermann, Synlett, 2002, 1855.
16. For the syntheses of natural products by cobalt mediated [2+2+2] cycloadditions, see: (±)-strychnine: M. J. Eichberg, R. L. Dorta, K. Lamottke and K. P. C. Vollhardt, Org. Lett., 2000, 2, 2479; (±)-LSD: C. Saá, D. D. Crotts, G. Hsu and K. P. C. Vollhardt, Synlett, 1994, 487; (+)-γ-lycorane: D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 1993, 579; (±)-illudol: E. P. Johnson and K. P. C. Vollhardt, J. Am. Chem. Soc., 1991, 113, 381; dl-estrone: R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 5253.
17. For the syntheses of natural products by cobalt mediated [2+2+2] cycloadditions, see: (±)-strychnine: M. J. Eichberg, R. L. Dorta, K. Lamottke and K. P. C. Vollhardt, Org. Lett., 2000, 2, 2479; (±)-LSD: C. Saá, D. D. Crotts, G. Hsu and K. P. C. Vollhardt, Synlett, 1994, 487; (+)-γ-lycorane: D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 1993, 579; (±)-illudol: E. P. Johnson and K. P. C. Vollhardt, J. Am. Chem. Soc., 1991, 113, 381; dl-estrone: R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 5253.
18. For the syntheses of natural products by cobalt mediated [2+2+2] cycloadditions, see: (±)-strychnine: M. J. Eichberg, R. L. Dorta, K. Lamottke and K. P. C. Vollhardt, Org. Lett., 2000, 2, 2479; (±)-LSD: C. Saá, D. D. Crotts, G. Hsu and K. P. C. Vollhardt, Synlett, 1994, 487; (+)-γ-lycorane: D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 1993, 579; (±)-illudol: E. P. Johnson and K. P. C. Vollhardt, J. Am. Chem. Soc., 1991, 113, 381; dl-estrone: R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 5253.
19. For the syntheses of natural products by cobalt mediated [2+2+2] cycloadditions, see: (±)-strychnine: M. J. Eichberg, R. L. Dorta, K. Lamottke and K. P. C. Vollhardt, Org. Lett., 2000, 2, 2479; (±)-LSD: C. Saá, D. D. Crotts, G. Hsu and K. P. C. Vollhardt, Synlett, 1994, 487; (+)-γ-lycorane: D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 1993, 579; (±)-illudol: E. P. Johnson and K. P. C. Vollhardt, J. Am. Chem. Soc., 1991, 113, 381; dl-estrone: R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 5253.
20. For the syntheses of natural products by cobalt mediated [2+2+2] cycloadditions, see: (±)-strychnine: M. J. Eichberg, R. L. Dorta, K. Lamottke and K. P. C. Vollhardt, Org. Lett., 2000, 2, 2479; (±)-LSD: C. Saá, D. D. Crotts, G. Hsu and K. P. C. Vollhardt, Synlett, 1994, 487; (+)-γ-lycorane: D. B. Grotjahn and K. P. C. Vollhardt, Synthesis, 1993, 579; (±)-illudol: E. P. Johnson and K. P. C. Vollhardt, J. Am. Chem. Soc., 1991, 113, 381; dl-estrone: R. L. Funk and K. P. C. Vollhardt, J. Am. Chem. Soc., 1980, 102, 5253.
21. For intramolecular alkyne cyclotrimerisations mediated by stoichiometric amounts of a nickel(0)-complex, see: P. Bhatarah and E. H. Smith, J. Chem. Soc., Perkin Trans. 1, 1992, 2163.
22. D. Felix, J. Schreiber, G. Ohloff and A. Eschenmoser, Helv. Chim. Acta, 1971, 54, 2896.
23. I. Fleming and E. Martínez de Marigorta, J. Chem. Soc., Perkin. Trans. 1, 1999, 889.
24. C. Hubschwerlen, Synthesis, 1986, 962; S. Takano, H. Numata and K. Ogasawara, Heterocycles, 1982, 19, 327.
25. C. Hubschwerlen, Synthesis, 1986, 962; S. Takano, H. Numata and K. Ogasawara, Heterocycles, 1982, 19, 327.
26. M. E. Jung and T. J. Shaw, J. Am. Chem. Soc., 1980, 102, 6304;
27. D. Y. Jackson, Synth. Commun., 1988, 18, 337.