title: Chemoenzymatic synthesis of the enantiomer of 4,12-dihydroxysterpurene, the structure assigned to a metabolite isolated from the culture broth of Stereum purpureum.
abstract: 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 broth of Stereum purpureum.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Ping
authors.initials: P
authors.lastname: Lan
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D031994:Sorbus / Q000382:microbiology; D013237:Stereoisomerism
chemical_list: C000595749:4,12-dihydroxysterpurene; D001688:Biological Products; D012717:Sesquiterpenes; C473358:sterpurene