Abstract
A novel strategy to N-Boc-N-methyl--tryptophans (abrine derivatives) was developed that relies on the palladium-catalyzed annulation of ortho-iodoanilines 12 with either N-Boc-N-methyl-propargylglycine 16 or aldehyde 11. Both 11 and 16 can be prepared from d-serine. An alternative route to propargylglycine 16 utilizes an enantioselective propargylation reaction of glycine imine 17.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetaldehyde / chemistry*
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Acetylene / chemistry*
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Aniline Compounds / chemistry*
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Indole Alkaloids / chemical synthesis*
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Indole Alkaloids / chemistry*
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Molecular Structure
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Palladium / chemistry*
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Tryptophan / analogs & derivatives*
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Tryptophan / chemistry*
Substances
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Aniline Compounds
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Indole Alkaloids
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Palladium
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Tryptophan
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Acetaldehyde
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Acetylene
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abrine