Synthesis of stereochemically diverse cyclic analogs of tubulysins

Yunjeong Park, Song Yi Bae, Jung Mi Hah, Sang Kook Lee, Jae Sang Ryu

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.

Original languageEnglish
Pages (from-to)6827-6843
Number of pages17
JournalBioorganic and Medicinal Chemistry
Volume23
Issue number21
DOIs
StatePublished - 1 Nov 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

  • Antitumor agents
  • Asymmetric catalysis
  • Hetero Diels-Alder reaction
  • Peptides
  • Tubulysin

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