An eight-step gram-scale synthesis of (-)-jiadifenolide

Nat Chem. 2015 Jul;7(7):604-7. doi: 10.1038/nchem.2283. Epub 2015 Jun 15.

Abstract

Development of a biologically active secondary metabolite into a useful medicine requires continuous access to meaningful quantities of material. Although any chemical synthesis is broadly useful for its versatility, identification of a synthesis route that can be economically scaled represents a greater challenge. Here we report a concise synthesis of the neurotrophic trace metabolite (-)-jiadifenolide and its production on a gram-scale. The brevity of the route and the structural similarity of a key intermediate to many potent Illicium terpenes make chemical synthesis the unquestionable method for accessing and modifying these potential therapeutics.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Molecular Structure
  • Sesquiterpenes / chemical synthesis*
  • Stereoisomerism

Substances

  • Sesquiterpenes
  • jiadifenolide

Associated data

  • PubChem-Substance/251912573
  • PubChem-Substance/251912574
  • PubChem-Substance/251912575
  • PubChem-Substance/251912576
  • PubChem-Substance/251912577
  • PubChem-Substance/251912578
  • PubChem-Substance/251912579
  • PubChem-Substance/251912580
  • PubChem-Substance/251912581
  • PubChem-Substance/251912582
  • PubChem-Substance/251912583
  • PubChem-Substance/251912584