My best try was to use aldol condensation after the reduction of the substrate(cyclopentanol) but that gives me a product with a methylphenyl substituent(2-Phenylcyclopentanone), nor a phenyl only.
1) oxidise using your favourite method (pyridinium dichromate; metal catalyst and oxygen; hypochlorous acid etc.) to cyclopentanone. 2) Pd catalysis using a bidentate ligand e.g. DPPF, with a hindered base, coupling the cyclopentanone to PhBr, to give the alpha-arylated product. See JACS 1997, 119, p.12382 by John Hartwig. This method works with isopropyl ketones also