Synthesis of Nemorosone via a Difficult Bridgehead Substitution Reaction

Nigel Simpkins, James Taylor, Michael Weller, CJ Hayes

Research output: Contribution to journalArticle

29 Citations (Scopus)


The synthesis of nemorosone, a polyprenylated acylphloroglucinol isolated from Clusia rosea, was achieved by means of a bridgehead substitution process, involving initial iodination and subsequent lithium-iodine exchange followed by acylation. The difficulties in the bridgehead substitution are discussed, and a probable explanation proposed, based on molecular modelling.
Original languageEnglish
Pages (from-to)639-643
Number of pages5
Issue number4
Publication statusPublished - 1 Mar 2010


  • nemorosone
  • iodine-lithium exchange
  • bridgehead substitution
  • B3LYP calculations


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