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Total Synthesis of 7‐ and 8‐Oxygenated Pyrano[3,2‐<i>a</i>]carbazole and Pyrano[2,3‐<i>a</i>]carbazole Alkaloids via Boronic Acid‐Catalyzed Annulation of the Pyran Ring
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2014
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HeterocyclicBoronic Acid‐catalyzed AnnulationMedicineCorresponding Carbazole PrecursorTotal SynthesisOrganic ChemistryPyran RingBoronic Acid-catalyzed AnnulationShort RouteChemistryHeterocycle ChemistryPharmacologySynthetic ChemistryDrug DiscoveryNatural Product Synthesis
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.
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