Total Synthesis of KingianinsA, D, and F

Total Synthesis of KingianinsA, D, and F

A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-04, Vol.52 (15), p.4221-4224
Hauptverfasser: Drew, Samuel L, Lawrence, Andrew L, Sherburn, Michael S
Format: Artikel
Sprache:eng
Schlagworte:
Closures
Dimerization
Precursors
Reduction
Synthesis
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Beschreibung
Zusammenfassung:A synthesis fit for a king: The total synthesis of (±)-kingianinsA, D, and F has been achieved in ten steps. Key features include the gram-scale synthesis and partial reduction of a conjugated tetrayne to a (Z,Z,Z,Z)-tetraene, the domino 8π-6π electrocyclic ring closure of a (Z,Z,Z,Z)-tetraene, and the radical-cation-catalyzed formal Diels-Alder dimerization of functionalized bicyclo[4.2.0]octadiene precursors.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201210084