Abstract
AbstractTreatment of the tosylate of khusiol with lithium carbonate in aqueous 1,4‐dioxane affords, via a Wagner–Meerwein rearrangement, (+)‐prezizanol. POCl3/pyridine‐mediated dehydration of (+)‐prezizanol then gives (+)‐prezizaene. More direct and efficient routes to this last compound were achieved by treating either khusiol or its C8 epimer with POCl3/pyridine. Under related conditions, a cyclic sulfate is converted, by a high yielding process, into an alcohol that embodies the decahydro‐1,7‐methanonaphthalene framework.
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