Synthesis of a cyclic analogue of Tuv N-methyl tubulysin

Yunjeong Park, Jae Kyun Lee, Jae Sang Ryu

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Abstract Tubulysins are the most potent antimitotic agents known so far. We are interested in the conformational effect of tubulysin and herein we report the design and synthesis of a conformationally rigid cyclic analogue of Tuv N-methyl tubulysin. A conformationally rigid tetrahydropyran moiety was incorporated into the Tuv fragment via enantioselective hetero Diels-Alder reaction to prevent the rotation of the Tuv chain. The following diastereoselective reductive amination yielded the (4-methylamino)tetrahydropyranyl Tuv fragment, which was coupled to d-Mep-l-Ile dipeptide fragment and Tup fragment sequentially.

Original languageEnglish
Article numberst-2014-u0031-l
Pages (from-to)1063-1068
Number of pages6
Issue number8
StatePublished - 9 Mar 2015

Bibliographical note

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© Georg Thieme Verlag.


  • Diels-Alder reaction
  • antitumor agents
  • asymmetric catalysis
  • asymmetric synthesis
  • medicinal chemistry
  • peptides


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