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Synfacts 2009(9): 0939-0939
DOI: 10.1055/s-0029-1217621
DOI: 10.1055/s-0029-1217621
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Sporolide B
Rezensent(en):Philip KocienskiK. C. Nicolaou*, Y. Tang, J. Wang
The Scripps Research Institute, La Jolla and University of California, San Diego, USA
Total Synthesis of Sporolide B
Angew. Chem. Int. Ed. 2009, 48: 3449-3453
The Scripps Research Institute, La Jolla and University of California, San Diego, USA
Total Synthesis of Sporolide B
Angew. Chem. Int. Ed. 2009, 48: 3449-3453
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. August 2009 (online)
Key words
sporolide B - [2+2+2] cycloaddition - intramolecular Diels-Alder reaction - ortho-quinones - ruthenium
Significance
Sporolide B is a marine metabolite with no apparent biological activity. The Scripps synthesis uses a ruthenium-catalyzed [2+2+2] cycloaddition to generate the chlorinated arene ring in G and an intramolecular Diels-Alder reaction of the ortho-quinone H.
Comment
The excellent diastereoselectivity in the Diels-Alder reaction is due to the steric bias arising from the two oxygen substituents in the dienophile. However, the regioselectivity of the reaction is harder to explain.