A convenient route for the preparation of title compounds from benzopyran-4-one (1) and its corresponding 3,3-2H2 deuterated analogue (2) is reported. Treatment of 1 or 2 with lithium aluminum deuteride followed by dehydration afforded, respectively, 4-2H precocene (3c) or 3,4-2H2 precocene (3b). Likewise, reduction of 2 with lithium aluminum hydride and subsequent dehydration led to the formation of 3-2H precocene (3d). Finally, the corresponding 3,4-epoxy derivatives of all these compounds were prepared in good yields by conventional procedures.
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