- Synthesis of novel alpha-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus.
Synthesis of novel alpha-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus.
Bioscience, biotechnology, and biochemistry (2002-11-27)
Toshio Nishikawa, Kyoko Wada, Minoru Isobe
PMID12450149
ZUSAMMENFASSUNG
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.
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