Synthesis of D-abrines by palladium-catalyzed reaction of ortho-iodoanilines with N-Boc-N-methylalanyl-substituted acetaldehyde and acetylene

Org Lett. 2013 May 17;15(10):2474-7. doi: 10.1021/ol4009409. Epub 2013 Apr 30.

Abstract

A novel strategy to N-Boc-N-methyl--tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / chemistry*
  • Acetylene / chemistry*
  • Aniline Compounds / chemistry*
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Molecular Structure
  • Palladium / chemistry*
  • Tryptophan / analogs & derivatives*
  • Tryptophan / chemistry*

Substances

  • Aniline Compounds
  • Indole Alkaloids
  • Palladium
  • Tryptophan
  • Acetaldehyde
  • Acetylene
  • abrine