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Synlett 2001; 2001(11): 1723-1726
DOI: 10.1055/s-2001-18089
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Conversion of a Cyclic α,β-Unsaturated Ketone into a Tertiary Dienyl Hydroperoxide: Application to the First Hemisynthesis of 15-Hydroperoxyabietic Acid

Laure Haberkorn* , Vincent Mutterer, Elena Giménez Arnau, Jean-Pierre Lepoittevin
  • *Laboratoire de Dermatochimie, Université Louis Pasteur, Clinique Dermatologique, CHU, 67091 Strasbourg, France; Fax + 33(3)88 14 04 47; E-mail: jplepoit@chimie.u-strasbg.fr
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Publication Date:
29 October 2001 (online)

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The first hemisynthesis of 15-hydroxyperoxyabietic acid, a major contact allergen among the oxidation products of colophony, is reported. The key step includes a new approach to easily obtain a dienyl tertiary hydroperoxide from a cyclic α,β-unsaturated ketone. The procedure is based on the formation of a bromodiene using a Vilsmeier's reagent, followed by a halogen/metal exchange and alkylation with acetone, to afford the dienyl alcohol precursor of the hydroperoxide.

colophony - 15-hydroperoxyabietic acid - dienyl hydroperoxide - α,β-unsaturated ketone - halo-diene alkylation

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