Tetrahedron Letters

Synthesis of the first fluorinated cantharidin analogues

M Essers, B Wibbeling, G Haufe

Index: Essers, Michael; Wibbeling, Birgit; Haufe, Guenter Tetrahedron Letters, 2001 , vol. 42, # 32 p. 5429 - 5433

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Citation Number: 46

Abstract

Fluorinated cantharidin analogues (4–7) have been synthesized for the first time. The key step in each synthesis is an exo-selective Diels–Alder reaction of furan with the appropriate fluorinated maleic anhydride. 17O NMR measurements of 5–7 and the corresponding non- fluorinated parent compounds were undertaken to show the influence of the fluorine substituent (s) on the electronic properties of the oxygen atoms.