Synthesis of highly functionalized cyclooctenes by ring-closing metathesis: Unexpected formation of a trans isomer

Angewandte Chemie (International Edition in English)

Volumn 39, Issue 4, 2000, Pages 726-728

  Bourgeois, Damien ^a   Pancrazi, Ange ^b   Ricard, Louis ^c   Prunet, Joëlle ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

^b Allée du Réseau Jean Marie Buckmaster   (France)

^c LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000037017     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (38)

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2. For the isolation of taxol, see M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325-2327. For total syntheses of taxol, see K. Morihara, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 12980-12981, and references therein. For the biological activity of taxol, see M. Suffness in Taxol: Science and Applications, CRC, Boca Raton, FL, 1995.
3. For the isolation of taxol, see M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon, A. T. McPhail, J. Am. Chem. Soc. 1971, 93, 2325-2327. For total syntheses of taxol, see K. Morihara, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 12980-12981, and references therein. For the biological activity of taxol, see M. Suffness in Taxol: Science and Applications, CRC, Boca Raton, FL, 1995.
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23. Abbreviations: Ac = acetate; Bz = benzoate; PG = protecting group; Tris = 2,4,6-triisopropylphenylsulfonyl; TES = triethylsilyl; TBAF = tetrabutylammonium fluoride.
24. A detailed analysis of the synthesis of the metathesis precursors will be reported elsewhere.
25. S. D. Edwards, T. Lewis, R. J. K. Taylor, Tetrahedron Lett. 1999, 40, 4267-4270.
26. Schrock's molybdenum catalyst was not used with 12, as it is known to be incompatible with free OH groups.
27. The stereochemistry of 13 was determined by correlation with (Z)-18, whose synthesis will be reported elsewhere.
28. 3. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-135213 and 135214. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
29. S. Mackay, C. J. Gilmore, C. Edwards, M. Tremayne, N. Stuart, K. Shankland, maXus: a computer program for the solution and refinement of crystal structures from diffraction data, University of Glasgow, Scotland, UK, Nonius BV, Delft, The Netherlands and MacScience Co. Ltd., Yokohama, Japan, 1998.
30. G. M. Sheldrick, SHELXL-97, Universität Göttingen, Germany, 1997.
31. The authors invoke an acid catalysis resulting from the use of dichloromethane as solvent, since the presence of triethylamine inhibits the formation of the isomerized product. In our case, the isomerization might result from the prolonged exposure of the product to the catalyst at high temperature: Grubbs observed isomerization of RCM products during distillation when residual amounts of the catalyst were present, see H. D. Maynard, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 4137-4140.
32. We thank Dr. Mahuteau for the complete structure determination of both diastereomers of 16.
33. K. C. Nicolaou, P. G. Nantermet, R. K. Guy, J. Chem. Soc. Chem. Commun. 1994, 295-296.
34. A. L. Spek, Platon, a Multipurpose Crystallographic Tool, Utrecht University, The Netherlands, 1999.
35. 3): δ = 154.2, 142.3, 137.5, 126.7, 125.4, 93.2, 82.7, 48.2, 43.4, 41.8, 36.2, 31.7, 26.2, 26.0, 24.8, 23.0, 22.0, 20.4, 17.6, 13.8.
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