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Synfacts 2012; 8(2): 0119
DOI: 10.1055/s-0031-1290180
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis and Structural Revision of the Piperarborenines

Contributor(s):
Steven V. Ley
,
Duncan L. Browne
Gutekunst WR, Baran PS * The Scripps Research Institute, La Jolla, USA
Total Synthesis and Structural Revision of the Piperarborenines via Sequential Cyclobutane C–H Arylation.

J. Am. Chem. Soc. 2011;
133: 19076-19079
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Further Information

Publication History

Publication Date:
19 January 2012 (online)

 
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Key words

C–H activation - cyclobutanes - piperarborenines

Significance

Isolated from the shrub Piper arborescens, the piperarborenines display in vitro cytotoxicity against cancer cell lines (P-388, HT-29 and A549). The piperarborenines feature a central cyclobutane core appended with both aromatic and imide groups.


 

Comment

Key to the synthesis of the proposed structure of piperarborenine D was the sequential C–H-activated arylation of a cyclobutane core (E → G and H → J). However, it was found that the true identity of piperarborenine D was that of a head-to-head [2+2] cycloaddition.


 

 


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