Mapping the Catechol Binding Site in Dopamine D1 Receptors: Synthesis and Evaluation of Two Parallel Series of Bicyclic Dopamine Analogues

✍ Scribed by Dr. Lisa A. Bonner; Dr. Uros Laban; Benjamin R. Chemel; Jose I. Juncosa; Prof. Markus A. Lill; Val J. Watts; Dr. David E. Nichols

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 596 KB
• Volume: 6
• Category: Article
• ISSN: 1860-7179
• DOI: 10.1002/cmdc.201100010

✦ Synopsis

Scheme 2. Synthesis of 2 a-c, e. Reagents and conditions: a) BF 3 •Et 2 O, Et 3 SiH, CH 2 Cl 2 , 08C, 1 h; b) BF 3 •Et 2 O, allylTMS, CH 2 Cl 2 , 258C, 2 h; c) CyMgCl or AdMgBr, 0 8C, 1 h; d) Mitsunobu conditions, 25 8C, 2 h; e) H 2 , Pd/C, EtOH, 1 atm, 25 8C, 24 h. Scheme 3. Attempted synthesis of phenyl-substituted chroman. Reagents and conditions: a) PhMgBr, 0 8C, 1 h, 85 %; b) SOCl 2 , pyridine, 0 8C, 5 min, 62 %; c) H 2 , catalyst, (see text).