Issue 27, 2014
From the journal:

Organic & Biomolecular Chemistry

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

Vivek Humne,a   Yuvraj Dangat,b   Kumar Vankab  and  Pradeep Lokhande*a  

* Corresponding authors

a Center for Advance Studies, Department of Chemistry, University of Pune, Pune, India
E-mail: vivekhumne@rediffmail.com, pdlokhande@chem.unichem.ac.in

b Division of Physical Chemistry, CSIR-National Chemical Laboratory, Pune, India

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/C4OB00635F
Article type
Communication
Submitted
25 Mar 2014
Accepted
24 Apr 2014
First published
24 Apr 2014

Org. Biomol. Chem., 2014,12, 4832-4836

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

V. Humne, Y. Dangat, K. Vanka and P. Lokhande, Org. Biomol. Chem., 2014, 12, 4832 DOI: 10.1039/C4OB00635F

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