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American Chemical Society, Journal of the American Chemical Society, 8(132), p. 2528-2529, 2010

DOI: 10.1021/ja9106572

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Total Synthesis of the Ammosamides

Journal article published in 2010 by Chambers C. Hughes, William Fenical ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

The ammosamides A-C are chlorinated pyrrolo[4,3,2-de]quinoline metabolites isolated from the marine-derived Streptomyces strain CNR-698. The natural products, which possess a dense array of heteroatoms, were synthesized in 17-19 steps from 4-chloroisatin. That the five nitrogen atoms were introduced at the appropriate time and in a suitable oxidation state was key to the success of the total synthesis. Compared to synthetic deschloro ammosamide B, natural ammosamide B is much less susceptible to oxidative degradation.