Synthesis of d‑Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with N‑Boc‑N‑methylalanyl-substituted Acetaldehyde and Acetylene

Synthesis of d‑Abrines by Palladium-catalyzed Reaction of ortho-Iodoanilines with N‑Boc‑N‑methylalanyl-substituted Acetaldehyde and Acetylene

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 propargyl...

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Veröffentlicht in:Organic letters 2013-05, Vol.15 (10), p.2474-2477
Hauptverfasser: Danner, Paulami, Morkunas, Marius, Maier, Martin E
Format: Artikel
Sprache:eng
Schlagworte:
Acetaldehyde - chemistry
Acetylene - chemistry
Aniline Compounds - chemistry
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Molecular Structure
Palladium - chemistry
Tryptophan - analogs & derivatives
Tryptophan - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4009409