Synthesis of pretubulysin-derivatives via the TubUgi-approach

Org Biomol Chem. 2015 Jun 7;13(21):6010-20. doi: 10.1039/c5ob00587f.

Abstract

The Ugi reaction is found to be a very powerful tool for the synthesis of (pre)tubulysin derivatives, allowing the introduction of various functionalized side chains in only one step. While polar groups such as amides are not well tolerated, unpolar side chains such as allyl or propargyl ether are well accepted. These functionalities also allow subsequent modifications in the side chain, e.g. via ring closing metathesis or Click reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry
  • Click Chemistry
  • Cyclization
  • Ethers / chemical synthesis
  • Ethers / chemistry
  • Myxococcales / chemistry*
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry

Substances

  • Alkynes
  • Ethers
  • Oligopeptides
  • propargyl ether
  • pretubulysin