Synthesis of (+)-crocacin D and simplified bioactive analogues

  • Bioorg Med Chem. 2015 Mar 1;23(5):1062-8. doi: 10.1016/j.bmc.2015.01.008.
Adele E Pasqua  1 ,  Frank D Ferrari  1 ,  James J Crawford  2 ,  William G Whittingham  3 ,  Rodolfo Marquez  4
Affiliations
  • 1. School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK.
  • 2. Department of Medicinal Chemistry, AstraZeneca R&D, Charnwood, Bakewell Rd., Loughborough LE11 5RH, UK.
  • 3. Syngenta, Jealott's Hill Research Station, Bracknell, Berkshire RG42 6EY, UK.
  • 4. School of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK. Electronic address: [email protected].
PMID: 25638500 DOI: 10.1016/j.bmc.2015.01.008
Abstract

The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting Materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported.

Keywords
Anti-fungal; Bio-active; Crocacins; Enamides; Nematocidal.
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