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Chemoenzymatic synthesis of the enantiomer of 4,12-Dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of stereum purpureum

Lan, Ping; Banwell, Martin; Willis, Anthony C.


Compound ent-1 has been prepared by engaging a derivative of the enantiomerically enriched and microbially derived cis-1,2-dihydrocatechol 6 in an intramolecular Diels-Alder reaction, elaboration of the adduct so-formed to the cyclopentannulated bicyclo[2.2.2]octenone 3, and photochemical rearrangement of this to the cyclobutanone 2. By such means it has been established that 4,12-dihydroxysterpurene (1) is not the structure of the natural product isolated by Xie and co-workers from a culture...[Show more]

CollectionsANU Research Publications
Date published: 2015
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol5034817


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