10.1021/ol0518840.s001 Robin A. Fairhurst Robin A. Fairhurst Diana Janus Diana Janus Annabel Lawrence Annabel Lawrence Synthesis of the Marine Sponge Derived β<sub>2</sub>-Adrenoceptor Agonist S1319 American Chemical Society 2005 adrenoceptor agonist S 1319 Marine Sponge Derived β 2 β 2 Adrenoceptor Agonist S 1319 cyclization precursor marine sponge butyl ether residue 2005-10-13 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Synthesis_of_the_Marine_Sponge_Derived_sub_2_sub_Adrenoceptor_Agonist_S1319/3263398 The marine sponge derived β<sub>2</sub>-adrenoceptor agonist S1319 has been synthesized following a six-step linear sequence. Central to the approach employed is the formation of a 7-lithiated-2,4-dialkoxybenzothiazole intermediate obtained via a directed-lithiation/benzyne-mediated cyclization reaction. The incorporation of a <i>tert-</i>butyl ether residue into the cyclization precursor for the pivotal ring-closing step has been shown to significantly increase the efficiency of the reaction by the suppression of a competing directed ortho-lithiation reaction.