title: Combining the power of Ti(III)-mediated processes for easy access to hydroxylated polycyclic terpenoids: synthesis of sesterstatin 1 and C-D rings of aspergilloxide.
abstract: A straightforward access to polyhydroxylated terpenoids based on two key titanocene(III)-mediated reactions is presented: the "head-to-tail" Barbier-type addition of prenyl chlorides to α,β-unsaturated aldehydes, which allows the introduction of hydroxy groups at desirable positions of the acyclic precursor, and the subsequent bioinspired radical cyclisation. This methodology has been also used in the first total synthesis of pentacyclic sesterstatin 1 and a model compound of the C-D rings of aspergilloxide.
authors.affiliation: Department of Organic Chemistry, University of Granada, Faculty of Sciences, Spain.
authors.forename: Tania
authors.initials: T
authors.lastname: Jiménez
authors.forename: Sara P
authors.initials: SP
authors.lastname: Morcillo
authors.forename: Ana
authors.initials: A
authors.lastname: Martín-Lasanta
authors.forename: Daniel
authors.initials: D
authors.lastname: Collado-Sanz
authors.forename: Diego J
authors.initials: DJ
authors.lastname: Cárdenas
authors.forename: Andreas
authors.initials: A
authors.lastname: Gansäuer
authors.forename: José
authors.initials: J
authors.lastname: Justicia
authors.forename: Juan M
authors.initials: JM
authors.lastname: Cuerva
mesh_terms: D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D014025:Titanium / Q000737:chemistry*
chemical_list: D004852:Epoxy Compounds; D009942:Organometallic Compounds; D011083:Polycyclic Compounds; D013729:Terpenes; C457039:aspergilloxide; C110787:sesterstatin 1; C406884:titanocene; D014025:Titanium