Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from D-serine

Published in: Journal, Volume : 22, Issue : 14-15, Pages : 1522-1529

DOI : 10.1016/j.tetasy.2011.08.014

Author : Malhotra, Rajesh; Ghosh, Amit; Ghosh, Rajib; Chakrabarti, Sagar; Dutta, Swarup; Dey, Tushar K.; Roy, Subho; Basu, Sourav; Hajra, Saumen

Abstract : A scalable asym. synthesis of trans-2-amino-6,7-dimethoxy-1-phenyltetralin and its N-nosyl derivative have been achieved from Garner aldehyde derived from easily available D-serine using a stereoselective PhMgBr addition, Wittig reaction and TFA-mediated Friedel-Crafts cyclization as the key steps. The synthesis of dihydrexidine is accomplished from the N-nosyl-2-amino-1-phenyltetralin.