First Total Synthesis of Tubulysin B

The first total synthesis of tubulysin B is described. The aziridine route to tubuphenylalanine (Tup) of the tubulysin D/U-series could not be transferred to the synthesis of tubutyrosine (blue moiety). Therefore, tubutyrosine (Tut) was synthesized by a Wittig olefination/diastereoselective catalyti...

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Bibliographic Details
Published in:Organic letters 2009-12, Vol.11 (24), p.5567-5569
Main Authors: Pando, Orlando, Dörner, Simon, Preusentanz, Rainer, Denkert, Annika, Porzel, Andrea, Richter, Wolfgang, Wessjohann, Ludger
Format: Article
Language:English
Subjects:
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Myxococcales - chemistry
Oligopeptides - chemical synthesis
Oligopeptides - chemistry
Oligopeptides - pharmacology
Pipecolic Acids - chemical synthesis
Pipecolic Acids - chemistry
Pipecolic Acids - pharmacology
Stereoisomerism
Tubulin Modulators - chemical synthesis
Tubulin Modulators - chemistry
Tubulin Modulators - pharmacology
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Summary:The first total synthesis of tubulysin B is described. The aziridine route to tubuphenylalanine (Tup) of the tubulysin D/U-series could not be transferred to the synthesis of tubutyrosine (blue moiety). Therefore, tubutyrosine (Tut) was synthesized by a Wittig olefination/diastereoselective catalytic reduction sequence. Interestingly, the C-2 epimer of tubulysin B has a cytotoxic activity almost identical to the natural diastereomer.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902320w