Bioscience, Biotechnology, and Biochemistry 2002-10-01

Synthesis of novel alpha-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus.

Toshio Nishikawa, Kyoko Wada, Minoru Isobe

Index: Biosci. Biotechnol. Biochem. 66(10) , 2273-8, (2002)

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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.