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Generation of (+)-prezizanol, (+)-prezizaene and the ent -β-isopipitzol framework via cationic rearrangement of khusiol and related compounds

Sharma, Mukesh; Banwell, Martin; Willis, Anthony


Treatment 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...[Show more]

CollectionsANU Research Publications
Date published: 2014
Type: Journal article
Source: Asian Journal of Organic Chemistry
DOI: 10.1002/ajoc.201400019


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