trans-2, 3-Dihydroxy-6a, 7, 8, 12b-tetrahydro-6 H-chromeno [3, 4-c] isoquinoline: Synthesis, Resolution, and Preliminary Pharmacological Characterization of a New …

…, G Giorgioni, RA Grubbs, BR Chemel…

Index: Cueva, Juan Pablo; Giorgioni, Gianfabio; Grubbs, Russell A.; Chemel, Benjamin R.; Watts, Val J.; Nichols, David E. Journal of Medicinal Chemistry, 2006 , vol. 49, # 23 p. 6848 - 6857

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Citation Number: 44

Abstract

We report the synthesis of trans-2, 3-dihydroxy-6a, 7, 8, 12b-tetrahydro-6 H-chromeno [3, 4- c] isoquinoline hydrochloride 6 and the resolution of its enantiomers. This new compound is an oxygen bioisostere of the potent dopamine D1-selective full agonist dihydrexidine. The initial synthetic approach involved, as a key step, a Suzuki coupling between a chromene triflate and a boronate ester, followed by isoquinoline formation and reduction of the ...