Concise total synthesis of (±)-aspidospermidine

Concise total synthesis of (±)-aspidospermidine

(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the...

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Veröffentlicht in:Organic & biomolecular chemistry 2015-05, Vol.13 (18), p.5255-5259
Hauptverfasser: Ma, Haichen, Xie, Xingang, Jing, Peng, Zhang, Weiwei, She, Xuegong
Format: Artikel
Sprache:eng
Schlagworte:
Carbon-13 Magnetic Resonance Spectroscopy
Indole Alkaloids - chemical synthesis
Indole Alkaloids - chemistry
Proton Magnetic Resonance Spectroscopy
Quinolines - chemical synthesis
Quinolines - chemistry
Spectrometry, Mass, Electrospray Ionization
Stereoisomerism
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Zusammenfassung:(±)-Aspidospermidine (1) has been synthesized from the commercially available 2,3-dihydro-1H-carbazol-4(9H)-one 6 in 10 steps with 20% overall yield. The key step of the strategy is a one-pot carbonyl reduction/iminium formation/intramolecular conjugate addition reaction that may be applied for the synthesis of other Aspidosperma alkaloids.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00228a