Issue 72, 2014
From the journal:

RSC Advances

Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues†

Mouhamad Jida,‡*a   Dirk Tourwé‡a  and  Steven Ballet‡*a  

* Corresponding authors

a Research Group of Organic Chemistry, Departments of Chemistry and Bio-engineering Sciences, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium
E-mail: mouhamad.jida@vub.ac.be, sballet@vub.ac.be

Abstract

A facile and efficient synthetic method for the stereoselective preparation of trisubstituted tetrahydro-β-carboline-fused diketopiperazine derivatives is reported. The methodology represents a one-pot four-step reaction, employing the Ugi four-component condensation which is followed by a Boc-deprotection, a Pictet–Spengler reaction and a final lactamization. All THBC-DKPs were obtained in good yields and excellent diastereomeric excess.

Graphical abstract: Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues

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Article information

DOI
https://doi.org/10.1039/C4RA05981F
Article type
Communication
Submitted
19 Jun 2014
Accepted
18 Aug 2014
First published
18 Aug 2014

RSC Adv., 2014,4, 38159-38163

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Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues

M. Jida, D. Tourwé and S. Ballet, RSC Adv., 2014, 4, 38159 DOI: 10.1039/C4RA05981F

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