4.7 Article

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

Journal

CHEMICAL COMMUNICATIONS
Volume 51, Issue 62, Pages 12427-12430

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc04500b

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Funding

  1. Danish Cancer Society
  2. Lundbeck Foundation (Lundbeckfoundation Fellow grant)
  3. Carlsberg Foundation
  4. Danish National Research Foundation
  5. Danish Research Council for Strategic Research/Natural Sciences
  6. Lundbeck Foundation [R105-2011-9308] Funding Source: researchfish

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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.

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