S1 Supporting Information Design and Synthesis of Cyclic RGD-Pentapeptoids by Consecutive Ugi Reactions Otilie E. Vercillo, †‡ Carlos Kleber Z. Andrade, ‡ and Ludger A. Wessjohann* † † Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, D-06120 Halle (Saale), Germany Fax: +49 345 5582 1309; Tel: +49 345 5582 1301; E-mail: wessjohann@ipb-halle.de ‡ Laboratório de Química Metodológica e Orgânica Sintética, Instituto de Química , Universidade de Brasília, CP 4478, 70910-970 Brasília-DF, Brazil. Table of Contents General Remarks S1 Experimental Section S2 General procedure for the Ugi reaction S2 General procedure for ester hydrolysis S2 General procedure for Cbz cleavage S2 General procedure for macrocyclization S3 Compounds data S3 Spectra of selected compounds S10 General Remarks All commercially available chemicals were used without further purification. Methanol HPLC grade was used in Ugi reactions. Analytical thin layer chromatography (TLC) was performed using silica gel 60 F 254 aluminum sheets and detected by UV absortion (254 nm) or by charring with a solution of (NH 4 ) 6 Mo 7 O 24 (25.0 g), Ce(SO 4 ) 2 (5.0 g) in concd. H 2 SO 4 (50 mL) and water (450 mL) or with a solution of ninhydrin in n-butanol (3:1 w/v) and 3% acetic acid. Flash column chromatography was performed using silica gel (0.040- 0.063