Abstract
Reaction of (+)-pin-2-ene (1) or (+)-trans-sobrerol (p-menth-6-ene-trans-2,8-diol)(3) with peroxysuccinic acid gives 6,8-epoxy-cis-p-menthane-trans-1,trans-2-diol (5a) and trans-p-menthane-cis-1,trans-2,trans-6,8-tetraol (6). Similarly, pinol (6,8-epoxy-p-menth-1-ene)(7) yields endo-2,endo-6-dihydroxycineol (1,8-epoxy-trans-p-menthane-trans-2,trans-6-diol)(15a) and trans-p-menthane-cis-1,trans-2,cis-6,8-tetraol (16). Hydrolysis of pinol trans-epoxide (trans-1,trans-2:6,8-diepoxy-cis-p-menthane)(12) with water also gives the diol (15a), oxidation of which gives 2,6-dioxocineol (1,8-epoxy-p-menthane-2,6-dione)(17) and endo-2-hydroxy-6-oxocineol (1,8-epoxy-trans-6-hydroxy-p-menthan-2-one)(18a). Borohydride reduction of compound (17) affords exo-2,exo-6-dihydroxycineol (1,8-epoxy-p-menthane-cis-2,cis-6-diol)(19a) and the endo-2-hydroxy-isomer (20a); the hydroxy-ketone (18a) similarly yields only compound (15a).
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