Synthesis of the Marine Sponge Derived β2-Adrenoceptor Agonist S1319

Synthesis of the Marine Sponge Derived β2-Adrenoceptor Agonist S1319

The marine sponge derived β2-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 i...

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Bibliographic Details
Published in:Organic letters Vol. 7; no. 21; pp. 4697 - 4700
Main Authors: Fairhurst, Robin A, Janus, Diana, Lawrence, Annabel
Format: Journal Article
Language:English
Japanese
Published: American Chemical Society 13-10-2005
Online Access:Get full text
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Summary:The marine sponge derived β2-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 tert-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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0518840