Synthesis of novel alpha-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus.
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.
Nishikawa
Toshio
T
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
Wada
Kyoko
K
Isobe
Minoru
M
D000596:Amino Acids / Q000138:chemical synthesis*; D000814:Aniline Compounds / Q000737:chemistry; D002384:Catalysis; D003300:Copper; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D010165:Palladium; D012694:Serine / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D015032:Zinc
D000596:Amino Acids; D000814:Aniline Compounds; D006027:Glycosides; D007202:Indicators and Reagents; D007211:Indoles; D012694:Serine; D010165:Palladium; C075715:3-iodoaniline; D003300:Copper; D015032:Zinc