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  • Title: Diverging pathways to topologically complex polycyclic bis-acetals and their ring system interchange.
    Author: Castillo RR, Aquino M, Gandara Z, Safir I, Elkhayat Z, Retailleau P, Arseniyadis S.
    Journal: Org Lett; 2012 Mar 16; 14(6):1628-31. PubMed ID: 22394381.
    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).
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