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Synlett 2018; 29(08): 1076-1078
DOI: 10.1055/s-0036-1591942
letter
© Georg Thieme Verlag Stuttgart · New York

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

Rajashekar Kommera
a   Department of Chemistry, Jawaharlal Nehru Technological University College of Engineering, Hyderabad 500085, India
b   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Telangana 502307, India
,
Venkateshwer Reddy Kasireddy
c   Department of Chemistry, CMR Engineering College, Jawaharlal Nehru Technological University, Hyderabad 501401, India
,
Venkat Reddy Ghojala
b   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Telangana 502307, India
,
Markandeya Bekkam
b   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Telangana 502307, India
,
Pradeep Rebelli
b   Department of Research and Development, MSN R&D Center, Pashamylaram, Medak, Telangana 502307, India
,
Jayaprakash Rao Yerrabelly*
d   Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad 500004, India
e   Department of Organic Chemistry, Telangana University, Nizamabad, Telangana 503322, India   Email: yjpr_19@yahoo.com
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Further Information

Publication History

Received: 17 December 2017

Accepted after revision: 29 January 2018

Publication Date:
22 February 2018 (online)

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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 epothilone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591942.
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  • References and Notes

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