Piperitenone, epoxide

Access to 3-menthene-l,8-diol (670), one of the minor products isolated (as its 1-acetate) from incubation of 7-terpenyl acetate (671) with a suspension of cultured Nicotiana tabacum cells, was conveniently achieved by reduction of piperitenone epoxide (620) with lithium aluminum hydride. ... 

Essential oil composition studies of interest concern Mentha rotundifolia [—85% piperitenone epoxide (26)], Artemisia afra (cineole, artemisia ketone. 

The majority of this work is confined to the synthesis of the epoxy derivatives of natural terpenes bearing an exocyclic double bond (see table overleaf). The stereochemical course of the reaction is governed by the factors discussed in Section 4.5.1.3.1. Umbellulone 1 was smoothly converted under typical Weitz-Scheffer conditions to a single epoxyumbellulone 233. (+)-Pulegone 3 gave a mixture of cis- and /ram-epoxides in a ratio 64.5 35.5, while piperitenone oxide 6 yielded piperitenone dioxide 7 as the sole product34,35. Epoxidation of pinocarvone 8... 

Epoxidation of (+)-Piperitenone Oxide with Alkaline Hydrogen Peroxide Typical Procedure34 ... 

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