Diverging Pathways to Topologically Complex Polycyclic Bis-acetals and Their Ring System Interchange
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 protoco...
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| Veröffentlicht in: | Organic letters 2012-03, Vol.14 (6), p.1628-1631 |
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| creator | Castillo, Rafael R Aquino, Maurizio Gandara, Zoila Safir, Imad Elkhayat, Zobida Retailleau, Pascal Arseniyadis, Siméon |
| description | 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). |
| doi_str_mv | 10.1021/ol300388b |
| format | Article |
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| ispartof | Organic letters, 2012-03, Vol.14 (6), p.1628-1631 |
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| source | American Chemical Society; MEDLINE |
| subjects | Acetals - chemical synthesis Acetals - chemistry Alcohols - chemical synthesis Alcohols - chemistry Catalysis Chemical Sciences Molecular Structure Organic chemistry Oxidation-Reduction Polycyclic Aromatic Hydrocarbons - chemical synthesis Polycyclic Aromatic Hydrocarbons - chemistry Stereoisomerism |
| title | Diverging Pathways to Topologically Complex Polycyclic Bis-acetals and Their Ring System Interchange |
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