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Synthesis 1992; 1992(1/2): 101-105
DOI: 10.1055/s-1992-34169
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Natural Furanocembranoids. A Synthetic Approach to Lophotoxin based on an Acyl Radical Macrocyclisation Strategy

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

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A concise synthesis of the furan-containing macrocyclic (cembranoid) ring system 8 (10-isopropenyl-3,7,13-trimethyl-15-oxabicyclo [10.2.1]pentadeca-2,6, 12,14-tetraene) found in Iophotoxin (1) and other members of this family of irreversible nicotinic receptor antagonists, is described. The synthesis features a 14-endo trig cyclisation from an unsaturated acyl radical intermediate incorporating a terminal conjugated enone moiety, viz 10, leading to the macrocycle (5E,9E)-13-isopropenyl-2,6,10-trimethylcyclotetradeca-5, 9-diene-2,4-dione (9), followed by acid-catalysed furan ring formation from the resulting 1,4-dione system in 9 (Scheme 1).