Total Synthesis of (±)-Goniomitine via Radical Translocation

Total Synthesis of (±)-Goniomitine via Radical Translocation

The aspidosperma alkaloid goniomitine was synthesized in six steps from 2-ethyl-δ-valerolactam. The convergent strategy features an Ullman coupling to assemble the required carbon atoms. A complexity-generating radical translocation reaction was used to build the indole architecture.

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Veröffentlicht in:Organic letters 2015-09, Vol.17 (18), p.4558-4560
Hauptverfasser: Vellucci, Jessica K, Beaudry, Christopher M
Format: Artikel
Sprache:eng
Schlagworte:
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Lactams - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The aspidosperma alkaloid goniomitine was synthesized in six steps from 2-ethyl-δ-valerolactam. The convergent strategy features an Ullman coupling to assemble the required carbon atoms. A complexity-generating radical translocation reaction was used to build the indole architecture.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02277