Issue 40, 2012
From the journal:

Organic & Biomolecular Chemistry

Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue†

Dan Balan,a   Christopher J. Burns,bc   Nicholas G. Fisk,d   Helmut Hügel,*a   David C. S. Huang,bc   David Segal,bc   Charlotte White,d   Jörg Waglera  and  Mark A. Rizzacasa*d  

* Corresponding authors

a School of Applied Sciences [Applied Chemistry], RMIT University, Bowen Street, Melbourne, Vic. 3001, Australia

b Walter and Eliza Hall Institute of Medical Research, 1G Royal Parade, Parkville, Victoria, Australia

c Department of Medical Biology, The University of Melbourne, Parkville, Victoria, Australia

d School of Chemistry, the Bio21 Institute, The University of Melbourne, VIC 3010, Australia
E-mail: masr@unimelb.edu.au

Abstract

The first synthesis of a lactam analogue 3 of salicylihalamide A (1) is reported. A key step in the approach was a photochemical acylation coupling between amine 10 and dioxinone 9 to form the amide 19. Acetylation followed by RCM with Grubbs 1st generation catalyst gave the desired E-lactam 23 (E : Z ratio 87 : 13) as the major compound. Conversion of macrolactam 23 into the vinyl iodide 26 followed by Cu catalysed cross coupling with the diene amide 7 gave aza-salicylihalamide analogue 3 in good yield. This compound demonstrated potent activity against several human leukaemia cell lines.

Graphical abstract: Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue

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Article information

DOI
https://doi.org/10.1039/C2OB26649K
Article type
Paper
Submitted
15 Jun 2012
Accepted
24 Aug 2012
First published
28 Aug 2012

Org. Biomol. Chem., 2012,10, 8147-8153

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Synthesis and biological evaluation of a potent salicylihalamide A lactam analogue

D. Balan, C. J. Burns, N. G. Fisk, H. Hügel, D. C. S. Huang, D. Segal, C. White, J. Wagler and M. A. Rizzacasa, Org. Biomol. Chem., 2012, 10, 8147 DOI: 10.1039/C2OB26649K

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