An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin

Org Biomol Chem. 2015 Sep 7;13(33):8906-11. doi: 10.1039/c5ob01125f.

Abstract

We report an efficient Mukaiyama-aldol reaction of tryptanthrin with fluorinated enol silyl ethers, which is carried out in methanol without the use of any catalyst. This method is applied to the total synthesis of the difluoro analogues of the natural product Phaitanthrin B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Catalysis
  • Chemistry, Organic / methods*
  • Ethers / chemistry*
  • Halogenation*
  • Magnetic Resonance Spectroscopy
  • Quinazolines / chemistry*
  • Silanes / chemical synthesis*
  • Silanes / chemistry

Substances

  • Aldehydes
  • Biological Products
  • Ethers
  • Quinazolines
  • Silanes
  • tryptanthrine
  • 3-hydroxybutanal