Synthesis of novel alpha-C-glycosylamino acids and reverse regioselectivity in Larock's heteroannulation for the synthesis of the indole nucleus |
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| Authors: | Nishikawa Toshio Wada Kyoko Isobe Minoru |
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| Affiliation: | Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan. |
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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. |
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