Synthesis of supposed enone prodrugs of apomorphine and N-propyl-norapomorphine

We have previously demonstrated that the enone prodrug GMC-6650 acts as a highly efficient dopaminergic agonist. In vivo, this compound is bioactivated to its corresponding catecholamine, TL-334. The goal here was to investigate if this bioactivation also occurs for the supposed enone prodrug of apomorphine. We describe the 12-step synthesis of this supposed prodrug, 6-alkyl-5,6,6a,8,9,10-hexahydro-4H-dibenzo[de,g]quinolin-11(7H)-one (R=Me, n-Pr). (C) 2007 Elsevier Ltd. All rights reserved.