Cross coupling protocols were applied for the synthesis of 3-(4-heteroaryl-phenyl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters. Stille conditions produced the corresponding products in reasonable yields. Samarium iodide reduction of the resulting coupling products produced the 2 beta-carbomethoxy-3 alpha-aryl-8-oxabicyclo[3.2.1]octane diastereoisomers as the major, and the 2 beta-carbomethoxy-3 beta-aryl-8-oxabicyclo[3.2.1]octane diastereoisomer as the minor products. Both diastereomers manifested inhibition of the dopamine (DAT) and serotonin (SERT) transporters, with some selectivity for SERT inhibition. (c) 2005 Elsevier Ltd. All rights reserved.