Total Synthesis of the Indole Alkaloid (±)- and (+)-Methyl N-Decarbomethoxychanofruticosinate

Total Synthesis of the Indole Alkaloid (±)- and (+)-Methyl N-Decarbomethoxychanofruticosinate

All caged up: The first total synthesis of N‐decarbomethoxychanofruticosinate (see figure) is achieved by using a SmI2‐mediated intramolecular Reformatsky‐like reaction to create the seven‐membered ring, and an intramolecular oxidative coupling to install the caged and strained ring system.

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Veröffentlicht in:Angewandte Chemie International Edition 2013-12, Vol.52 (49), p.12988-12991
Hauptverfasser: Wei, Yi, Zhao, Duo, Ma, Dawei
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Cyclization
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
natural products
samarium
Stereoisomerism
strained molecules
total synthesis
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Zusammenfassung:All caged up: The first total synthesis of N‐decarbomethoxychanofruticosinate (see figure) is achieved by using a SmI2‐mediated intramolecular Reformatsky‐like reaction to create the seven‐membered ring, and an intramolecular oxidative coupling to install the caged and strained ring system.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201307788