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Synthesis 1988; 1988(12): 972-975
DOI: 10.1055/s-1988-27771
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Selective Synthesis of trans- and cis-p-Mentha-1,8-dien-5-ol from trans-Verbenol

Michel Bulliard* , Geneviève Balme, Jacques Goré
  • *Laboratoire de Chimie Organique I, UA 0467 du CNRS, Université Claude Bernard Lyon I. Escil 43 Bd du 11 Novembre 1918, F-69622 Villeurbanne Cedex, France
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Publication Date:
20 August 2002 (online)

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A selective synthesis of both trans- and cis- p-mentha-1,8-dien-5-ol from trans-verbenol is described. The sequence leading to trans-p-mentha-1,8-dien-5-ol consists of cleavage of the cyclobutane ring of pinene with N-bromosuccinimide in acetone to give the acetonide of 6-bromo-trans-p-menthene-5,8-diol, hydrodebromination with lithium aluminum hydride. and acidic treatment of the resultant acetonide of trans-p-menthene-5,8-diol. cis-p-Mentha-1,8-dien-5-ol is obtained by Swern oxidation of the trans-isomer and reduction of the resultant ketone with lithium tri-sec-butylborohydride. Acidic treatment of the acetonide of cis-p-menthene-5,8-diol (obtained from cis-verbenol) gives exclusively p-mentha-1(7),2-dien-8-ol.

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