5,6-Epoxy-5,6-dihydroisoquinoline 9 and 7,8-epoxy-7,8-dihydroisoquinoline 21 were each obtained by multi-step synthetic sequences from 5,6,7,8-tetrahydroisoquinoline 1. The mammalian metabolite, trans-5,6-dihydroisoquinoline-5,6-diol 10 was chemically synthesised by base-catalysed hydration of the isoquinoline arene oxide 9.
D. R. Boyd, R. J. H. Davies, L. Hamilton and J. J. McCullough, J. Chem. Soc., Perkin Trans. 1, 1992, 31 DOI: 10.1039/P19920000031
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