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Synthesis of the marine sponge derived beta2-adrenoceptor agonist S1319.

Fairhurst, Robin and Janus, Diana and Lawrence, Annabel (2005) Synthesis of the marine sponge derived beta2-adrenoceptor agonist S1319. Organic Letters, 7 (21). pp. 4697-4700. ISSN 1523-7060

Abstract

[reaction: see text] The marine sponge derived beta2-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.

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Date Deposited: 14 Dec 2009 13:59
Last Modified: 14 Dec 2009 13:59
URI: https://oak.novartis.com/id/eprint/498

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