title: Asymmetric total synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether via ACC alkylation and evaluation of their anti-HIV activity.
abstract: The total asymmetric synthesis of (+)- and (-)-clusianone and (+)- and (-)-clusianone methyl enol ether is reported. Asymmetric induction is achieved through the use of ACC alkylation, providing the key intermediates with an er of 99:1. The four synthetic compounds were evaluated for their anti-HIV activity. Both (+)- and (-)-clusianone displayed significant anti-HIV activity.
authors.affiliation: Department of Chemistry, Duke University, Durham, NC 27705, USA.
authors.forename: Michelle R
authors.initials: MR
authors.lastname: Garnsey
authors.forename: James A
authors.initials: JA
authors.lastname: Matous
authors.forename: Jesse J
authors.initials: JJ
authors.lastname: Kwiek
authors.forename: Don M
authors.initials: DM
authors.lastname: Coltart
mesh_terms: D000478:Alkylation; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D004987:Ethers / Q000737:chemistry*; D006678:HIV / Q000187:drug effects*; D006801:Humans; D013237:Stereoisomerism
chemical_list: C118110:7-epiclusianone; D019380:Anti-HIV Agents; D001577:Benzophenones; D016227:Benzoquinones; D001643:Bridged Bicyclo Compounds; D004987:Ethers