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Preparation of precocene 2 and 3 4 epoxyprecocene 2 deuterated analogs at carbon 3 carbon 4 and carbon 3 carbon 4

, : Preparation of precocene 2 and 3 4 epoxyprecocene 2 deuterated analogs at carbon 3 carbon 4 and carbon 3 carbon 4. Zeitschrift fuer Naturforschung Teil B Anorganische Chemie Organische Chemie 40(4): 556-558

A convenient route for the preparation of title compounds from benzopyran-4-one (1) and its corresponding 3,3-2H2 deuterated analog (2) is reported. Treatment of 1 or 2 with lithium aluminium 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. [The use of these compounds in biorational insect control strategies is discussed.].

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