Total Synthesis of 7- and 8-Oxygenated Pyrano[3,2-a]carbazole and Pyrano[2,3-a]carbazole Alkaloids via Boronic Acid-Catalyzed Annulation of the Pyran Ring

The boronic acid‐catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine‐D is available in only three steps and 55% overall yield from the corresponding carbazole precursor. Efficient process: The boronic acid‐catalyzed...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-07, Vol.20 (28), p.8536-8540
Main Authors: Julich-Gruner, Konstanze K., Kataeva, Olga, Schmidt, Arndt W., Knölker, Hans-Joachim
Format: Article
Language:English
Subjects:
Alkaloids
Alkaloids - chemical synthesis
Boronic Acids - chemistry
Carbazoles
Carbazoles - chemical synthesis
Carbazoles - chemistry
Catalysis
Chemical reactions
Chemistry
Citral
Cyclization
CH bond activation
Molecular Structure
natural products
Organic chemistry
Oxygenated
palladium
Precursors
Pyrans
Stereoisomerism
stereoselective catalysis
Synthesis
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Summary:The boronic acid‐catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine‐D is available in only three steps and 55% overall yield from the corresponding carbazole precursor. Efficient process: The boronic acid‐catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine‐D is available in only three steps and 55 % overall yield from the corresponding carbazole precursor.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201403143