title: Diverging pathways to topologically complex polycyclic bis-acetals and their ring system interchange.
abstract: Carbinol-tethered octalin-diols (1), which differ only by the C11 configuration at the angular position, were transformed selectively to three types of structurally unrelated original scaffolds such as unsymmetrical octahydroanthracenes (5/7), furofuranes (6), or spirans (8/9) via a two-step protocol. The 11S* configuration ensures a C13-C4 Friedel-Crafts type C-C bonding (through an unprecedented oxidative cleavage-triggered domino process) while the 11R* configuration allows for a C13-C2 Marson-type Friedel-Crafts C-C bonding (through a nucleophilic acetal opening).
authors.affiliation: Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette Cedex, France.
authors.forename: Rafael R
authors.initials: RR
authors.lastname: Castillo
authors.forename: Maurizio
authors.initials: M
authors.lastname: Aquino
authors.forename: Zoila
authors.initials: Z
authors.lastname: Gandara
authors.forename: Imad
authors.initials: I
authors.lastname: Safir
authors.forename: Zobida
authors.initials: Z
authors.lastname: Elkhayat
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Siméon
authors.initials: S
authors.lastname: Arseniyadis
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000438:Alcohols; D011084:Polycyclic Aromatic Hydrocarbons