An Expedient Synthesis of a Functionalized Core Structure of Bielschowskysin

Photons in action: Cascade sequences, brevity, and efficiency are the hallmarks of the synthesis of a functionalized tricyclo[9.3.0.0]tetradecane ring system of the marine natural product bielschowskysin. The synthesis is achieved in five steps, with the key step being an exquisite intramolecular [2...

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Veröffentlicht in:	Angewandte Chemie International Edition 2011-05, Vol.50 (22), p.5149-5152
Hauptverfasser:	Nicolaou, K. C., Adsool, Vikrant A., Hale, Christopher R. H.
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkanes - chemistry Animals Anthozoa - chemistry antimalarial agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - toxicity Crystallography, X-Ray cytotoxic agents Diterpenes - chemical synthesis Diterpenes - chemistry Diterpenes - toxicity Macrocyclic Compounds - chemistry Molecular Conformation natural products photocycloaddition Plasmodium falciparum - drug effects
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Beschreibung
Zusammenfassung:	Photons in action: Cascade sequences, brevity, and efficiency are the hallmarks of the synthesis of a functionalized tricyclo[9.3.0.0]tetradecane ring system of the marine natural product bielschowskysin. The synthesis is achieved in five steps, with the key step being an exquisite intramolecular [2+2] photocycloaddition of a macrocyclic precursor (see scheme).
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201101360