The chromium-Reformatsky reaction: Asymmetric synthesis of the aldol fragment of the cytotoxic epothilons from 3-(2-bromoacyl)-2-oxazolidinones

Tetrahedron Letters

Volumn 38, Issue 8, 1997, Pages 1363-1366

  Gabriel, Tobias ^a   Wessjohann, Ludger ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EPOTHILONE A; EPOTHILONE B;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031584942     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02494-X     Document Type: Article

References (30)

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2. 1. Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569; Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560-563; tubulin-stabilization: Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325-2333.
3. 1. Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569; Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560-563; tubulin-stabilization: Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325-2333.
4. 1. Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569; Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560-563; tubulin-stabilization: Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325-2333.
5. 2. Reviews: Schinzer, D. Eur. Chem. Chron. 1996, 1, 7-10; Wessjohann, L. Angew. Chem. 1997, submitted.
6. 2. Reviews: Schinzer, D. Eur. Chem. Chron. 1996, 1, 7-10; Wessjohann, L. Angew. Chem. 1997, submitted.
7. 3. Balog, A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J.; Danishefsky, S. J. Angew. Chem. 1996, 108, in press.
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9. 4. Nicolaou, K. C.; He, Y.; Vourlourais, D.; Vallberg, H.; Yang, Z. Angew. Chem. 1996, 108, 2554-2556; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399-2401.
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13. 7. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. 1994, 106, 38-69; Angew. Chem. Int. Ed. Engl. 1994, 33, 45; Wessjohann, L. Angew. Chem. 1994, 106, 1011-1013; Angew. Chem. Int. Ed. Engl. 1994, 33, 959-961.
14. 7. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. 1994, 106, 38-69; Angew. Chem. Int. Ed. Engl. 1994, 33, 45; Wessjohann, L. Angew. Chem. 1994, 106, 1011-1013; Angew. Chem. Int. Ed. Engl. 1994, 33, 959-961.
15. 7. Nicolaou, K. C.; Dai, W.-M.; Guy, R. K. Angew. Chem. 1994, 106, 38-69; Angew. Chem. Int. Ed. Engl. 1994, 33, 45; Wessjohann, L. Angew. Chem. 1994, 106, 1011-1013; Angew. Chem. Int. Ed. Engl. 1994, 33, 959-961.
16. 8. Wessjohann, L.; Wild, H. Synthesis 1997, accepted; Wessjohann, L. A.; Gabriel, T. J. Org. Chem. 1997, submitted; Gabriel, T.; Wessjohann, L. Aldol Reactions Made Irreversible by an Intrinsic Kinetic Quench: The Chromium Reformatsky Reaction. In 11th International Conference On Organic Synthesis (ICOS-11); KNCV and IUPAC Eds.; H. Hiemstra (Amsterdam Institute of Molecular Studies): Amsterdam, 1996; p. 317; Wessjohann, L.; Mühlbauer, A. Chrom(II)-vermittelte Reaktionen vom Reformatsky Typ: Lösungsmitteleinfluß, Regio-und Diastereoselektivität. In 24. GDCh-Hauptversammlung Hamburg; GDCh Ed.; VCH: Weinheim, 1993; p. 502.
17. 8. Wessjohann, L.; Wild, H. Synthesis 1997, accepted; Wessjohann, L. A.; Gabriel, T. J. Org. Chem. 1997, submitted; Gabriel, T.; Wessjohann, L. Aldol Reactions Made Irreversible by an Intrinsic Kinetic Quench: The Chromium Reformatsky Reaction. In 11th International Conference On Organic Synthesis (ICOS-11); KNCV and IUPAC Eds.; H. Hiemstra (Amsterdam Institute of Molecular Studies): Amsterdam, 1996; p. 317; Wessjohann, L.; Mühlbauer, A. Chrom(II)-vermittelte Reaktionen vom Reformatsky Typ: Lösungsmitteleinfluß, Regio-und Diastereoselektivität. In 24. GDCh-Hauptversammlung Hamburg; GDCh Ed.; VCH: Weinheim, 1993; p. 502.
18. 8. Wessjohann, L.; Wild, H. Synthesis 1997, accepted; Wessjohann, L. A.; Gabriel, T. J. Org. Chem. 1997, submitted; Gabriel, T.; Wessjohann, L. Aldol Reactions Made Irreversible by an Intrinsic Kinetic Quench: The Chromium Reformatsky Reaction. In 11th International Conference On Organic Synthesis (ICOS-11); KNCV and IUPAC Eds.; H. Hiemstra (Amsterdam Institute of Molecular Studies): Amsterdam, 1996; p. 317; Wessjohann, L.; Mühlbauer, A. Chrom(II)-vermittelte Reaktionen vom Reformatsky Typ: Lösungsmitteleinfluß, Regio-und Diastereoselektivität. In 24. GDCh-Hauptversammlung Hamburg; GDCh Ed.; VCH: Weinheim, 1993; p. 502.
19. 8. Wessjohann, L.; Wild, H. Synthesis 1997, accepted; Wessjohann, L. A.; Gabriel, T. J. Org. Chem. 1997, submitted; Gabriel, T.; Wessjohann, L. Aldol Reactions Made Irreversible by an Intrinsic Kinetic Quench: The Chromium Reformatsky Reaction. In 11th International Conference On Organic Synthesis (ICOS-11); KNCV and IUPAC Eds.; H. Hiemstra (Amsterdam Institute of Molecular Studies): Amsterdam, 1996; p. 317; Wessjohann, L.; Mühlbauer, A. Chrom(II)-vermittelte Reaktionen vom Reformatsky Typ: Lösungsmitteleinfluß, Regio-und Diastereoselektivität. In 24. GDCh-Hauptversammlung Hamburg; GDCh Ed.; VCH: Weinheim, 1993; p. 502.
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21. 9. Braun, M. Formation of C-C Bonds by Addition of Enolates to Carbonyl Groups: α-Unsubstituted Amide and Imide Enolates. In (Houben-Weyl: Methods in Organic Chemistry) Stereoselective Synthesis; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21b; pp. 1656-1660; Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
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23. 10. Sauer, J. C.; Sheehan, J. C.; Gilmont, E. R. Org. Synth., Colt. Vol. 1963, 4, 813-815; Skoldinov, A. P.; Arendaruk, A. P.; Godzhello, T. M. J. Org. Chem. USSR (Engl. Transl.) 1970, 6, 421-426. CAUTION, explosive hazard from propargyl aldehyde, e. g. with bases!
24. 11. Cf. also Kende, A. S.; Kawamura, K.; Orwat, M. J. Tetrahedron Lett. 1989, 30, 5821-5824.
25. 12. By analogy to similar compounds in this series S-stereochemistry can be assumed for C-β.
26. 13. Cf. Evans, D. A.; Bender, S. L. Tetrahedron Lett. 1986, 27, 799-802.
27. 14. Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099-3111.
28. 15. Inukai, T.; Yoshizawa, R. J. Org. Chem. 1967, 32, 404-407.
29. 3) (for the (R)-enantiomer, assignment deducted from 11). Analysis of the enantiomeric ratio was possible with derivative 16 by GC on 25 m 2,6-pentyl-4-butyryl-β-cyclodextrin (70% in OV 1701). We wish to thank Prof. Dr. W. König, Hamburg, for his support.
30. 17. Evans, D. A.; Clark, S. J.; Mettemich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.