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.