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Synfacts 2008(3): 0226-0226
DOI: 10.1055/s-2008-1042663
DOI: 10.1055/s-2008-1042663
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New YorkSynthesis of (±)-Communesin F
Contributor(s):Philip KocienskiJ. Yang, H. Wu, L. Shen, Y. Qin*
Sichuan University, Chengdu, P. R. of China
Total Synthesis of (±)-Communesin F
J. Am. Chem. Soc. 2007, 129: 13794-13795
Sichuan University, Chengdu, P. R. of China
Total Synthesis of (±)-Communesin F
J. Am. Chem. Soc. 2007, 129: 13794-13795
Further Information
Publication History
Publication Date:
21 February 2008 (online)
Key words
Heck reaction - Claisen rearrangement - cyclopropane cleavage
Significance
Qin and co-workers have accomplished the synthesis of heptacyclic communesin F (a Penicillium metabolite) in 23 steps (3% overall). The two adjacent quaternary centers were constructed sequentially by a carbene insertion to give A and a Claisen rearrangement (C→D).
Comment
The cyclization (F→G) was accompanied by 26% of a butadiene derived from elimination. The Heck reaction (E→F) was performed neat under microwave heating. This is the first synthesis of a member of the communesin family.