Direct Synthesis of (+)-Erogorgiaene through a Kinetic Enantiodifferentiating Step

Direct Synthesis of (+)-Erogorgiaene through a Kinetic Enantiodifferentiating Step

The combined approach of CH activation and a Cope rearrangement catalyzed by a rhodium catalyst [Rh2(R‐dosp)4] (dosp=(N‐dodecylbenzenesulfonyl)prolinate) is shown to be a very effective method for the construction of the three stereogenic centers (marked in red, see scheme) present in the diterpene...

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Veröffentlicht in:Angewandte Chemie International Edition 2005-03, Vol.44 (11), p.1733-1735
Hauptverfasser: Davies, Huw M. L., Walji, Abbas M.
Format: Artikel
Sprache:eng
Schlagworte:
Crystallography, X-Ray
CH activation
Diterpenes - chemical synthesis
enantioselectivity
Kinetics
natural products
terpenoids
total synthesis
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Zusammenfassung:The combined approach of CH activation and a Cope rearrangement catalyzed by a rhodium catalyst [Rh2(R‐dosp)4] (dosp=(N‐dodecylbenzenesulfonyl)prolinate) is shown to be a very effective method for the construction of the three stereogenic centers (marked in red, see scheme) present in the diterpene erogorgiaene (1).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200462227