Functionalized, Enantiomerically Pure [2.1.1]-, [2.2.1]-, and [2.2.2]-Triblattanes†
Dipl.-Chem. Hermann Müller
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDipl.-Chem. Johann-Peter Melder
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDr. Wolf-Dieter Fessner
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDr. Dieter Hunkler
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorProf. Dr. Hans Fritz
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorCorresponding Author
Prof. Dr. Horst Prinzbach
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)Search for more papers by this authorDipl.-Chem. Hermann Müller
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDipl.-Chem. Johann-Peter Melder
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDr. Wolf-Dieter Fessner
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorDr. Dieter Hunkler
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorProf. Dr. Hans Fritz
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Search for more papers by this authorCorresponding Author
Prof. Dr. Horst Prinzbach
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)
Chemisches Laboratorium der Universität, Institut für Organische Chemie und Biochemie, Albertstr. 21, D-7800 Freiburg (FRG)Search for more papers by this authorThis work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and BASF AG.
Graphical Abstract
Triblattanes, such as the previously known 1—(+)-1 is shown here—are very promising, novel cage molecules. For example, 1 can be transformed efficiently into [2.2.2]-triblattatriene (+)-/(-)-2, a C14H14 pentacyclic compound, by means of a threefold ring expansion. Like its similarly obtained tribenzo derivative, 2 has D3 symmetry. The chemical versatility of 2 and its precursors is exemplified by the generation of the hexaketone 3, which was trapped as its triquinoxaline derivative.
References
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The Cs-symmetrical 3,8,14,18-tetraoxaoctacyclo[8.7.1.02, 4.05, 16.06, 12.07, 9-011, 17.013, 15]octadecane II (C14H14O4), formed on cleavage of one of the three bisallylic CC single bonds, has been identified.
