Issue 40, 2015
From the journal:

Organic & Biomolecular Chemistry

Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B†

Rodolfo Tello-Aburto,*a   Liam P. Hallada,ab   Doleshwar Niroulaa  and  Snezna Rogeljb  

* Corresponding authors

a Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA
E-mail: rtello_a@nmt.edu

b Department of Biology, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA

Abstract

The absolute stereochemistry of the cystargolides was determined by total synthesis. Evaluation of synthetic cystargolides and derivatives showed that the natural (2S,3R) stereochemistry is essential for activity. Moreover, benzyl esters (−)-10 and (−)-15 were found to be about 100 times more potent, and to selectively kill MCF-7 cancerous cells.

Graphical abstract: Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B

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Article information

DOI
https://doi.org/10.1039/C5OB01821H
Article type
Communication
Submitted
31 Aug 2015
Accepted
12 Sep 2015
First published
17 Sep 2015

Org. Biomol. Chem., 2015,13, 10127-10130

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Total synthesis and absolute stereochemistry of the proteasome inhibitors cystargolides A and B

R. Tello-Aburto, L. P. Hallada, D. Niroula and S. Rogelj, Org. Biomol. Chem., 2015, 13, 10127 DOI: 10.1039/C5OB01821H

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