Abstract
An alpha-C-iodoethynylglucose derivative was coupled with an L-serine-derived zinc-copper reagent to give alpha-C-glucosylpropargyl glycine, which underwent palladium catalyzed-heteroannulation with o-iodoaniline to give not alpha-C-glucosyl-tryptophan but alpha-C-glucosyl-iso-tryptophan. This is the first observation of complete reverse regioselectivity to Larock's proposal.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Amino Acids / chemical synthesis*
-
Aniline Compounds / chemistry
-
Catalysis
-
Copper
-
Glycosides / chemical synthesis*
-
Indicators and Reagents
-
Indoles / chemical synthesis*
-
Magnetic Resonance Spectroscopy
-
Optical Rotation
-
Palladium
-
Serine / chemistry
-
Spectrometry, Mass, Electrospray Ionization
-
Spectrophotometry, Infrared
-
Zinc
Substances
-
Amino Acids
-
Aniline Compounds
-
Glycosides
-
Indicators and Reagents
-
Indoles
-
Serine
-
Palladium
-
3-iodoaniline
-
Copper
-
Zinc