Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
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
Contributor(s):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
Further Information
Publication History
Publication Date:
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.