Common activated phenols, such as sesamol, undergo a one-pot annulation to hexahydrocannabinoids on being heated with citronellal, phenylboric acid and an excess of acetic acid. Benzodioxaborines 2 are shown to be intermediates and are proposed to undergo conversion into quinonemethides under the acid conditions employed. Generally the more stable equatorial-trans-stereoisomer is formed in better than 95% purity.
W. S. Mufphy, S. M. Tuladhar and B. Duffy, J. Chem. Soc., Perkin Trans. 1, 1992, 605 DOI: 10.1039/P19920000605
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