Towards a Synthesis of Epothilone A: Rapid Assembly of the C1-C6 and C7-C12 Fragments

Synlett

Volumn 1997, Issue 7, 1997, Pages 824-826

  De Brabander, Jef ^a   Rosset, Stephane ^a   Bernardinelli, Gérald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001149958     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-5757     Document Type: Article

References (27)

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2. L. M. Landino, T. L. MacDonald in The Chemistry and Pharmacology of Taxol® and its derivatives; V. Farin, Ed.; Elsevier: New York, 1995; Chapter 7, p 301.
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10. d) D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, ibid. 1997, 36, 523.
11. The ring-closing olefin metathesis reaction was also used for the synthesis of various desoxyepothilones, see: D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733.
12. For other studies in the epothilone field, see a) J. Mulzer, A. Mantoulidis, Tetrahedron Lett. 1996, 37, 9179; b) E. Claus, A. Pahl, P. G. Jones, H. M. Meyer, M. Kalesse, ibid. 1997, 38, 1359; c) T. Gabriel, L. Wessjohann, ibid. 1997, 38, 1363.
13. For other studies in the epothilone field, see a) J. Mulzer, A. Mantoulidis, Tetrahedron Lett. 1996, 37, 9179; b) E. Claus, A. Pahl, P. G. Jones, H. M. Meyer, M. Kalesse, ibid. 1997, 38, 1359; c) T. Gabriel, L. Wessjohann, ibid. 1997, 38, 1363.
14. For other studies in the epothilone field, see a) J. Mulzer, A. Mantoulidis, Tetrahedron Lett. 1996, 37, 9179; b) E. Claus, A. Pahl, P. G. Jones, H. M. Meyer, M. Kalesse, ibid. 1997, 38, 1359; c) T. Gabriel, L. Wessjohann, ibid. 1997, 38, 1363.
15. For the first total synthesis of epothilone B, see: D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T. C. Chou, L. He, S. B. Horwitz, Angew. Chem. Int. Ed. Engl. 1997, 36, 757.
16. a) W. Oppolzer, R. Moretti, S. Thomi, Tetrahedron Lett. 1989, 30, 5603;
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20. e) W. Oppolzer, P. Lienard, ibid. 1993, 34, 4321.
21. The diastereomeric ratio of 8 was determined by GC. The corresponding (2R)-diastereomer of 8 was prepared from alkylation of the lithium enolate of propionylbornane- 10,2-sultam with 1-bromo-4-pentene; see: A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942.
22. W. Oppolzer, C. Darcel, P. Rochet, S. Rosset, J. De Brabander, submitted for publication in Helv. Chim. Acta.
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24. Ketoaldehyde 10 was prepared according to a published procedure: T. Inukai, R. Yoshizawa, J. Org. Chem. 1967, 32, 404.
25. The boryl-enolate aldol reaction is more convenient and gives higher yields than the corresponding Mukayama-type aldol reaction of the O-silyl-N,O-ketene acetal derived from 9, described by: W. Oppolzer, C. Starkemann, Tetrahedron Lett. 1992, 33, 2439.
26. Crystallographic data of 11a have been deposited with the Cambridge Crystallographic Data Center, University Chemical Laboratory, 12 Union Road, Cambridge CB2 1EZ, England.
27. 3) 204.9, 138.2, 114.9, 46.2, 33.6, 30.3, 26.2, 13.3.