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Synlett 2018; 29(08): 1076-1078
DOI: 10.1055/s-0036-1591942
DOI: 10.1055/s-0036-1591942
letter
A Scalable Approach for the Synthesis of Epothilone Thiazole Fragment (C12–C21 unit) Via Wacker Oxidation
Authors
Weitere Informationen
Publikationsverlauf
Received: 17. Dezember 2017
Accepted after revision: 29. Januar 2018
Publikationsdatum:
22. Februar 2018 (online)
Abstract
A new scalable synthesis of the common thiazole fragment (C12–C21 unit) of epothilone family of molecules (epothilone A–D) has been developed via palladium-catalyzed Wacker oxidation as a key step using (S)-2,2,3,3,9,9,10,10-octamethyl-5-vinyl-4,8-dioxa-3,9-disilaundecane, which has been prepared from commercially available chiral synthon (R)-ethyl-4-cyano-3-hydroxybutanoate. Then further chemical modifications using Horner–Wadsworth–Emmons reaction and Wittig reaction result in the common thiazole fragment (C12–C21 unit) in good yields.
Key words
thiazole fragment - epothilone - Wacker oxidation - ixabepilone - C12–C21 unit of epothiloneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591942.
- Supporting Information (PDF)
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References and Notes
- 1 Newman DJ. Cragg GM. J. Nat. Prod. 2007; 70: 461
- 2 Höfle G. Bedorf N. Steinmetz H. Schomburg D. Gerth K. Reichenbach H. Angew. Chem. 1996; 35: 1567
- 3 Gerth K. Bedorf N. Höfle G. Irschik H. Reichenbach H. J. Antibiot. 1996; 49: 560
- 4 Cortes J. Baselga J. Oncologist 2007; 12: 271
- 5 Goodin S. Am. J. Health Syst. Pharm. 2008; 65: S10 (10 Supplement 3)
- 6 Schinzer D. Limberg A. Böhm OM. Chem. Eur. J. 1996; 2: 1477
- 7 Schinzer D. Limberg A. Böhm OM. Bauer A. Chem. Eur. J. 1999; 5: 2483
- 8 Nicolaou KC. Ninkovic S. Sarabia F. Vourloumis D. He Y. Vallberg H. Finlay MR.V. Yang Z. J. Am. Chem. Soc. 1997; 119: 7974
- 9 Taylor RE. Chen Y. Org. Lett. 2001; 3: 2221
- 10 Reiff EA. Nair SK. Narayan Reddy BS. Inagaki J. Henri JT. Greiner JF. Georg GI. Tetrahedron Lett. 2004; 45: 5845
- 11 For the import data and price of ethyl 4-cyano-3-hydroxybutanoate in India (Zauba), see: https://www.zauba.com/import-ethyl-4-cyano-3-hydroxy-butanoate-hs-code.html.
- 12 Soai K. Oyamada H. Ookawa A. Synth. Commun. 1982; 12: 463
- 13 Crimmins MT. Slade DJ. Org. Lett. 2006; 8: 2191
- 14 Tsuji J. Nagashima H. Nemoto H. Org. Synth., Coll. Vol. 7. 137. Wiley; New York: 1990
- 15 Smith III AB. Cho YS. Friestad GK. Tetrahedron Lett. 1998; 39: 8765
- 16 Schinzer D. Bauer A. Schieber J. Chem. Eur. J. 1999; 5: 2492