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Molecules 2008, 13(4), 995-1003; doi:10.3390/molecules13040995

Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1

1,* , 1, 1, 2 and 2
1 Department of Chemistry, University of Düsseldorf, Universitätstr. 1, D-40225 Düsseldorf, Germany 2 Max-Planck Research Unit for Enzymology of Protein Folding, Weinbergweg 22, D-06120 Halle, Germany
* Author to whom correspondence should be addressed.
Received: 3 April 2008 / Revised: 22 April 2007 / Accepted: 23 April 2008 / Published: 29 April 2008
(This article belongs to the Special Issue Spiro Compounds)
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The novel 3H-spiro[1-benzofuran-2-cyclopentan]-3-one skeleton has been madeaccessible by different routes. One- and two-step protocols lead to tricyclic and tetracyclicbenzofuranones 2 and 3, respectively. A four-step synthesis to spirocompound 4 isdescribed. The novel spirocyclic benzofuranones display modest to no inhibition of thehuman peptidyl prolyl cis/trans isomerase Pin1.
Keywords: Ketones; lithiation; cyclization; metathesis; spiroannulation Ketones; lithiation; cyclization; metathesis; spiroannulation
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Braun, M.; Hessamian-Alinejad, A.; De Lacroix, B.F.; Alvarez, B.H.; Fischer, G. Novel Spiroannulated 3-Benzofuranones. Synthesis and Inhibition of the Human Peptidyl Prolyl cis/trans Isomerase Pin1. Molecules 2008, 13, 995-1003.

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