title: A Short Synthesis of Aphanamol I in Both Racemic and Enantiopure Forms.
abstract: A short synthesis of the biologically active sesquiterpene natural product (+)-aphanamol I in both racemic and enantiopure forms is reported. Key steps include: a catalytic enantioselective conjugate addition, an oxidative radical cyclization, and a ring-expanding Claisen rearrangement.
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.
authors.forename: Steven J
authors.initials: SJ
authors.lastname: Ferrara
authors.affiliation: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. jonathan.burton@chem.ox.ac.uk.
authors.forename: Jonathan W
authors.identifier: http://orcid.org/0000-0002-5181-5301
authors.initials: JW
authors.lastname: Burton
mesh_terms: D001688:Biological Products; D002384:Catalysis; D003500:Cyclization; D010084:Oxidation-Reduction; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D012717:Sesquiterpenes; C413803:aphanamol I
keywords: Claisen rearrangement; aphanamol; conjugate addition; radical cyclization; total synthesis