title: Oxidative Entry into the Illicium Sesquiterpenes: Enantiospecific Synthesis of (+)-Pseudoanisatin.
abstract: Illicium sesquiterpenes have been the subject of numerous synthetic efforts due to their ornate and highly oxidized structures as well as significant biological activities. Herein we report the first chemical synthesis of (+)-pseudoanisatin from the abundant feedstock chemical cedrol (∼$50 USD/kg) in 12 steps using extensive site-selective C(sp3)-H bond functionalization. Significantly, this work represents a novel oxidative strategic template for future approaches to these natural products and their analogs.
authors.affiliation: Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
authors.forename: Kevin
authors.initials: K
authors.lastname: Hung
authors.affiliation: Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
authors.forename: Matthew L
authors.initials: ML
authors.lastname: Condakes
authors.affiliation: Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Morikawa
authors.affiliation: Department of Chemistry, University of California-Berkeley , 826 Latimer Hall, Berkeley, California 94720, United States.
authors.forename: Thomas J
authors.identifier: 0000-0001-5823-692X
authors.initials: TJ
authors.lastname: Maimone
mesh_terms: D060326:Chemistry Techniques, Synthetic; D029523:Illicium / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D012717:Sesquiterpenes; D013141:Spiro Compounds; C031244:anisatin