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Chemoenzymatic total syntheses of the sesquiterpene (-)-patchoulenone

Banwell, Martin; Hockless, David; McLeod, Malcolm

Description

The bicyclo[5.3.1]undec-7(8)-en-3-one 6, which is prepared from the monochiral cis-1,2-dihydrocatechol 4, affords a mixture of products 7, 8 and 9 on exposure to protic acid. Each of compounds 8 and 9 rearranges to congener 7 on treatment with SnCl2 or upon sustained reaction with protic acid. Reaction of the last compound with hydrogen in the presence of palladium on carbon affords a mixture of the saturated diols 10 and 11 with the latter capable of elaboration to (-)-patchoulenone (1) in...[Show more]

CollectionsANU Research Publications
Date published: 2003
Type: Journal article
URI: http://hdl.handle.net/1885/85800
Source: New Journal of Chemistry
DOI: 10.1039/b206372g

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