title: Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors.
abstract: cis-Dihydrocatechols, derived from biological cis-dihydroxylation of methyl benzoate, iodobenzene and benzonitrile, using the microorganism Pseudomonas putida UV4, were converted into pericosines A, C, and B, respectively. This approach constitutes the shortest syntheses, to date, of these important natural products with densely packed functionalities.
authors.affiliation: School of Chemistry and Chemical Engineering, Queen's University of Belfast, Belfast BT9 5AG, United Kingdom.
authors.forename: Derek R
authors.initials: DR
authors.lastname: Boyd
authors.forename: Narain D
authors.initials: ND
authors.lastname: Sharma
authors.forename: Carmen A
authors.initials: CA
authors.lastname: Acaru
authors.forename: John F
authors.initials: JF
authors.lastname: Malone
authors.forename: Colin R
authors.initials: CR
authors.lastname: O'Dowd
authors.forename: Christopher C R
authors.initials: CC
authors.lastname: Allen
authors.forename: Paul J
authors.initials: PJ
authors.lastname: Stevenson
mesh_terms: D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D012765:Shikimic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009281:Naphthalenes; C523077:methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate; C496389:pericosine B; C544052:pericosine C; C507866:trans-1,2-dihydro-1,2-naphthalenediol; D012765:Shikimic Acid