A Scalable Approach for the Synthesis of Epothilone Thiazole Fragment (C12–C21 unit) Via Wacker Oxidation

Abstract A new scalable synthesis of the common thiazole fragment (C 12 –C 21 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 be...

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Bibliographic Details
Published in:Synlett 2018-05, Vol.29 (8), p.1076-1078
Main Authors: Kommera, Rajashekar, Kasireddy, Venkateshwer Reddy, Ghojala, Venkat Reddy, Bekkam, Markandeya, Rebelli, Pradeep, Yerrabelly, Jayaprakash Rao
Format: Article
Language:English
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Summary:Abstract A new scalable synthesis of the common thiazole fragment (C 12 –C 21 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 (C 12 –C 21 unit) in good yields.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1591942