title: An Efficient Enantioselective Synthesis of the D1 Agonist (5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia- 5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929).
abstract: (5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia-5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929, 1), a potent selective dopamine D1 agonist, was synthesized enantioselectively from D-aspartic acid. Key features of the 10-step synthesis are the following: (1) there is no chromatography required; (2) formation of 15 occurs in >99% ee; (3) the electrophilic cyclization to provide the desired trans stereochemisry in 18 is achieved with no loss of enantiomeric integrity.
authors.affiliation: Neuroscience Research Division, Pharmaceutical Product Discovery, Department 47C, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, Illinois 60064-3500.
authors.forename: Paul P.
authors.initials: PP
authors.lastname: Ehrlich
authors.forename: Jeffrey W.
authors.initials: JW
authors.lastname: Ralston
authors.forename: Michael R.
authors.initials: MR
authors.lastname: Michaelides