Total Synthesis of (−)-Melotenine A

Total Synthesis of (−)-Melotenine A

'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to pr...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-08, Vol.52 (32), p.8309-8311
Hauptverfasser: Zhao, Senzhi, Sirasani, Gopal, Vaddypally, Shivaiah, Zdilla, Michael J., Andrade, Rodrigo B.
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids
annulation
Biological Products - chemical synthesis
Biological Products - chemistry
heterocycles
natural products
Secologanin Tryptamine Alkaloids - chemical synthesis
Secologanin Tryptamine Alkaloids - chemistry
total synthesis
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Beschreibung
Zusammenfassung:'Melo' out: A concise asymmetric synthesis of (−)‐melotenine A has been accomplished in fourteen steps and 1 % overall yield from commercial N‐tosylindole‐3‐carboxaldehyde. Key steps include a Piers annulation, an intermolecular vinylogous aldol reaction, and a novel one‐pot sequence to prepare the ABCE tetracycle. Boc=tert‐butoxycarbonyl, Ts=4‐toluenesulfonyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201302517