title: First total synthesis of (-)-achilleol B: reassignment of its relative stereochemistry.
abstract: The first total synthesis of (-)-achilleol B was achieved using a convergent approach with a longest linear sequence of 14 steps. Three key steps were employed, including an enantioselective Robinson annelation for the construction of the bicyclic moiety. The monocyclic synthon was prepared through a Ti(III)-mediated cylization of a chiral monoepoxide obtained via asymmetric dihydroxylation of geranylacetone. The asymmetric preparation of these subunits also permitted us to achieve the enantioselective synthesis of elegansidiol, achilleol A, and farnesiferol B.
authors.affiliation: Department of Organic Chemistry, Institute of Biotechnology, University of Granada, Granada, Spain.
authors.forename: Jesús F
authors.initials: JF
authors.lastname: Arteaga
authors.forename: Victoriano
authors.initials: V
authors.lastname: Domingo
authors.forename: José F
authors.initials: JF
authors.lastname: Quílez del Moral
authors.forename: Alejandro F
authors.initials: AF
authors.lastname: Barrero
mesh_terms: D031162:Achillea / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*; D014315:Triterpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013729:Terpenes; D014315:Triterpenes; C530507:achilleol B; C009884:geranylacetone