Issue 33, 2012
From the journal:

RSC Advances

Construction of tetrahydro-β-carboline skeletons via Brønsted acid activation of imidecarbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A†

Selvaraj Mangalaraja  and  Chinnasamy Ramaraj Ramanathan*a  

* Corresponding authors

a Department of Chemistry, Pondicherry University, Puducherry – 605 014, India
E-mail: crrnath.che@pondiuni.edu.in
Fax: +91-413-2656740
Tel: +91-413-2654416

Abstract

Indole, a π-nucleophile, reacts with Brønsted acid activated imide carbonyl group in an intramolecular fashion via a 6-exo-trig cyclization, to deliver a condensed tetrahydro-β-carboline unit. This methodology is effectively applied to assemble the tetrahydro-β-carboline skeleton containing alkaloids such as harmicine and 10-desbromoarborescidine-A.

Graphical abstract: Construction of tetrahydro-β-carboline skeletons via Brønsted acid activation of imide carbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A

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Article information

DOI
https://doi.org/10.1039/C2RA21734A
Article type
Communication
Submitted
08 Aug 2012
Accepted
24 Sep 2012
First published
25 Sep 2012

RSC Adv., 2012,2, 12665-12669

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Construction of tetrahydro-β-carboline skeletons via Brønsted acid activation of imide carbonyl group: syntheses of indole alkaloids (±)-harmicine and (±)-10-desbromoarborescidine-A

S. Mangalaraj and C. R. Ramanathan, RSC Adv., 2012, 2, 12665 DOI: 10.1039/C2RA21734A

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