Issue 109, 2015

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

Abstract

A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.

Graphical abstract: An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

Supplementary files

Article information

Article type
Paper
Submitted
12 Aug 2015
Accepted
14 Oct 2015
First published
15 Oct 2015

RSC Adv., 2015,5, 90121-90126

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

A. Kamal, M. Sathish, A. V. G. Prasanthi, J. Chetna, Y. Tangella, V. Srinivasulu, N. Shankaraiah and A. Alarifi, RSC Adv., 2015, 5, 90121 DOI: 10.1039/C5RA16221A

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