Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: a combined experimental and computational investigation

Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: a combined experimental and computational investigation

A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This met...

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Veröffentlicht in:Organic & biomolecular chemistry 2014-07, Vol.12 (27), p.4832-4836
Hauptverfasser: Humne, Vivek, Dangat, Yuvraj, Vanka, Kumar, Lokhande, Pradeep
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Carbazoles - chemical synthesis
Carbazoles - chemistry
Catalysis
Computer Graphics
Iodine - chemistry
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Zusammenfassung:A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00635f