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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
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
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