A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation

Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization i...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 34; pp. 7105 - 7108
Main Authors Ivanov, Andrey S., Zhalnina, Anna A., Shishkov, Sergey V.
Format Journal Article
LanguageEnglish
Russian
Published OXFORD Elsevier Ltd 22.08.2009
Elsevier
Subjects
Bortezomib
Chemistry
Chemistry, Organic
Convergent synthesis
Peptide coupling
Physical Sciences
PS-341
Racemization
Science & Technology
TBTU
TBTU
Racemization
Bortezomib
PS-341
Convergent synthesis
Peptide coupling
PROTEASOME
INHIBITORS
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Summary:Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization in the fragment condensation. In comparison with the original synthesis, the presented one is shorter by two steps, higher in yield, and provides better atom economy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.06.042