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Synlett 1991; 1991(5): 335-336
DOI: 10.1055/s-1991-34727
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Acyl Radical Macrocyclisations. A Synthesis of the Furanocembrane Unit in Lophotoxin and Pukalide

Martin P. Astley* , Gerald Pattenden
  • *Department of Chemistry, The University, Nottingham NG7 2RD, England
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Publication Date:
07 March 2002 (online)

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A concise synthesis of the furanocembrane unit 5 (10-isopropenyl-3,7,13-trimethyl-15-oxabicyclo[10.2.1]pentadeca-2,6,12,14-tetraene) found in the neurotoxin lophotoxin 3 and the related pukalide 4 is described. The synthesis uses a tandem intramolecular cyclisation strategy and the novel acyl radical macrocyclisation 7 → 6, as key features.

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