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Chem Commun (Camb). 2015 Aug 11;51(62):12427-30. doi: 10.1039/c5cc04500b.

The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile--development of a general synthetic strategy.

Author information

1
Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark. thpou@chem.au.dk.

Abstract

We demonstrate that a unique class-defining functionality (mc-APD) found in macrocyclic natural products with potent anti-cancer activity, imparts these compounds with electrophilic reactivity. The mc-APD group represents an interesting structural hybrid between canonical biologically relevant Michael-acceptors. Further, a novel thiol-elimination method for preparation of the mc-APD group is outlined.

PMID:
26146360
DOI:
10.1039/c5cc04500b
[Indexed for MEDLINE]

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