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

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

1,* , 1, 1, 2 and 2
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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Abstract

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 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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