Isotopic labelling shows that enzymic removal of the 1′-pro-S-hydrogen from an o-prenylated phenol correlates with the E-methyl of the latter becoming the pro-R-methyl at 6′ of the chromen produced; overall, the reaction is of limited stereoselectivity as deguelin cyclase does not specifically recognise the 1′-pro-S- or pro-R-hydrogens for removal.
P. Bhandari, N. Van Bruggen, L. Crombie and D. A. Whiting, J. Chem. Soc., Chem. Commun., 1989, 982 DOI: 10.1039/C39890000982
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